CREW Chase Sapphire Reserve v. Churn/Award Travel Crew

JeffSTL

OT Supporter
Aug 26, 2004
16,524
Illinois
I do travel a lot for work and fly primarily United. Sometimes I do fly Delta or Aeromexico though.

I mainly stay at IHG hotels, but I am lifetime Diamond with Hilton.

National car rental.

I'm top tier super duper status with all, except for United. I'm only Premier 1K and not Global Services.

I mainly use company card, but occasionally use my United card and accumulate about $8k a month in it, and pay it as expense reports clear (which is within 18 days).
Most of that is outside of my wheelhouse but kind of as general knowledge

United points tend to be valued at anywhere from 1.3-2.5 depending on if you use them for economy or biz and when you book. Chase has an IHG card, but the card/IHG program is often looked at as meh. Amex has all the Hilton cards. Lots of travelers love Hyatt, but they arent everywhere a Marriott/Hilton property is.

Its recommended to start with Chase cards as they have a 5/24 rule. That means you can only have 5 personal cards opened in the last 24 months from anywhere. Once you get to 5, they wont approve you for a single card they have. So if you start with Chase and open a few cards over the next couple years, then you could move on to Amex. Biz cars dont count towards the 5/24, but you cant open one if you are already 5/24. Biz cards have the best bonuses for sure. You dont really need a business to get a business card. We can help you with that a little when the time comes. I opened all 3 Chase biz cards under my SSN as a sole prop, then went and got an EIN # and have 2/3 business cards through that. Anyone can get an EIN and Chase has no idea what I do or dont do or make or dont make. 3 Ink bonuses add up to 250k Chase points, only 1 has a $95 annual fee. Chase points are worth 1.5-20 cents each and can be redeemed for much higher than that too.

Chase Transfer partners include:
Hyatt
Southwest
United
Virgin
Air Canada
Jet Blue
Singapore Airlines (awesome because you can transfer to SA and then use those points to book on several of their partner airlines like Alaska or any Star Alliance for cheaper than any other route)
British Airways

You can use their travel portal to book about anything, the current backbone is Expedia. The Sapphire cars are there premium/travel cards. You need a Sapphire card or a Ink Preferred biz card to be able to transfer points out to a partner. Chase Sapphire Reserve is the big dick daddy card. Has lost a ton of its value over the years. $550 AF, first $300 towards travel is reimbursed and they even count things like parking and tolls as travel. So basically the AF is $250 at most before all other perks and credits. All travel on the Sapphire Reserve (CSR) card earns 3x for all travel, the Chase Sapphire Preferred earns 2x. They just added a thing where you can earn 5x on flights and 10x on hotels if they are booked through the Chase portal. Also, they added something called Pay Yourself Back. With PYB you can use your points to pay off your statement at higher values. Right now the CSR you can pay off your dining purchases with points being worth 1.5x. I've been doing that a lot lately, and did it a ton when they had grocery as a PYB category. When you use the Chase travel portal to book travel you don't earn nights/miles or have access to any of your program perks with the airline or hotel. So not everyone uses or loves the portal. It is handy when you need a flight outside of your main places instead of straight cash, especially if you are redeeming points at 1.5x. It is a 3rd party booking so it may be a bitch with cancelations etc too. I've run into that. The CSP makes your points worth 1.25x booking through the Chase portal, and the CSR makes them worth 1.5x. Thats pretty nice. CSR gets you credit for Global Entry, Priority Pass for a lot of lounge access. CSP occasionally has a 100k sign up bonus (SUB) which just ended. Its down to 60k now. CSR's SUB is usually weaker at 50k. All Chase cards earn 3x on restaurants. All non sapphire cards earn 3x at pharmacies.

Chase Freedom Unlimited CFU- earns 1.5x on everything. 20k SUB and you earn 5x at all grocery stores for 12 months up to a total of $12k. The grocery part is pretty sweet. Thats
Chase Freedom Flex CFF- Same 20k/5x grocery SUB. 1x on everything, 5x on rotating categories each quarter. Usually stuff like gas, WalMart, grocery, PayPal, home improvement stores, warehouse stores, streaming, restaraunts, Amazon etc

Remember all the earn rates I quoted are either what you can transfer out with a CSP/CSR/CIP, or with a CSP your points/earn rate is worth 1.25x of what I said, and with the CSR they are worth 1.5x. So these earn rates are worth a lot more than what I listed depending on where you transfer them to or what card you use to book travel with through Chase. You can do things like buy gift cards at wherever the 5x bonus is. Buy amazon gift cards, gas gift cards, whatever. One of the business cards earns 5x at office stores and they sell gift cards to a ton of places including Amazon and apple. So you can *always* get 5x on every purchase from Amazon or Apple and anything. A further hack is they sell Visa Gift cards. Occasionally there is a promo where if you spend $300 on them, you get $15 off. I just bought 2 $200 VGCs for $398.50. They run this promo fairly often. So you can get 5x on damn near every purchase you make really. Put even fucking dime you can on your cards. I have my Mom/stepdad and Dad/stepmom using my cards as AUs, and occasionally get some from of my GFs spend.

As much as you travel you should be able to kill it with this stuff. I'd start with one of the CFU or CFF cards. I'd say do them back to back, but it may be hard for you to spend a full $24k at grocery stores in a year. Depending on how soon you want to travel using points, you could make your 2nd card a CSR/CSP. Run 100% of stuff through your cards and get paid back from work. The big bucks are made with sign up bonuses, but you dont want to "abuse" the system. Dont apply for too many cards too quick. People who abuse the system have been booted. As much spend as you can generate, you should be able to kick ass from earn rates too. Hopefully this post helps with a base layer with whatever you didnt know. It may be a bit jumbled as I typed it while watching football and went back and inserted some sentences in random places. And yes I'm autistic when it comes to this stuff and have nothing better to do. Oh, and when you go to signup for a card, PM me and I'll send you a referral link so I'll get some bonus points if they have one for whatever card. I can include nudes in said PM.
 
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JeffSTL

OT Supporter
Aug 26, 2004
16,524
Illinois
Oh boy. Good Luck with the audit.
@Hisma
I need to talk to a kick ass tax attorney. I do/actually will have a legit business now and watching YouTube videos from tax guys I know theres gotta be some things I can do to help me. Went to my moms CPA and he was just like nope. Maybe didnt give me the best advice for trust related things either. Been trying to help my dad get a trust done, and setup myself as some kind of business and I feel like I'm getting conflicting or not the best tax planning advice from either, especially compared to what tax attorneys who seem to really know their shit say on YouTube. Nobody hates the "but I saw on YouTube/online that..." more than me too. Sigh.
 

Hisma

OT Supporter
Apr 2, 2006
59,213
Reno, NV
@Hisma
I need to talk to a kick ass tax attorney. I do/actually will have a legit business now and watching YouTube videos from tax guys I know theres gotta be some things I can do to help me. Went to my moms CPA and he was just like nope. Maybe didnt give me the best advice for trust related things either. Been trying to help my dad get a trust done, and setup myself as some kind of business and I feel like I'm getting conflicting or not the best tax planning advice from either, especially compared to what tax attorneys who seem to really know their shit say on YouTube. Nobody hates the "but I saw on YouTube/online that..." more than me too. Sigh.
this space is so new the government has no fuckin clue how to handle this stuff. And with the completely anonymous nature of DEXs any yield farms, where the majority of my crypto income is made, I don't see this getting solved any time soon. There's no KYC so it doesn't really exist. Those that think I'm gonna get audited to hell don't know what they're talking about but it's funny that they think they understand.
I don't know what the nature of your business is. But if its crypto and you're not dealing with typical centralized exchanges with KYC, it's basically the wild west.
 

Soren

OT Supporter
Oct 9, 2002
36,738
My crypto portfolio is generating income in the ether that is the blockchain. So none of it is tracked / reported by say, coinbase or traditional crypto exchanges. The only evidence I have that crypto is making me money is when an ach lands in my bank account. So I can be creative with my reporting. Not trying to dodge taxes or anything, just trying to find a way to tell uncle Sam why there's a steady stream of money appearing in my bank account. Rather than just claiming cap gains, I'll reat it as business income.

The ach is attached to coinbase or whatever exchange is tied to your bank account. How do you explain that?
 

Soren

OT Supporter
Oct 9, 2002
36,738
The ach is attached to coinbase or whatever exchange is tied to your bank account. How do you explain that?

It's pretty straightforward. Money going out of exchange minus money going into exchange = gains. Probably your job to explain it as gifts/transfers etc.
 

Soren

OT Supporter
Oct 9, 2002
36,738
Sure. So you can avoid getting taxed when exchanging coins for other coins, but the withdrawal event will be flagged
 

Hisma

OT Supporter
Apr 2, 2006
59,213
Reno, NV
It's pretty straightforward. Money going out of exchange minus money going into exchange = gains. Probably your job to explain it as gifts/transfers etc.
exactly. but as I stated, those inflows/outflows do not come close to accounting for my actual gains. It's all almost all occurred outside of the boundaries of the exchange.
 

JeffSTL

OT Supporter
Aug 26, 2004
16,524
Illinois
this space is so new the government has no fuckin clue how to handle this stuff. And with the completely anonymous nature of DEXs any yield farms, where the majority of my crypto income is made, I don't see this getting solved any time soon. There's no KYC so it doesn't really exist. Those that think I'm gonna get audited to hell don't know what they're talking about but it's funny that they think they understand.
I don't know what the nature of your business is. But if its crypto and you're not dealing with typical centralized exchanges with KYC, it's basically the wild west.
No not at all. The only crypto I have interest in is buying and holding Bitcoin. They are gonna regulate the motherfuck out of stable coins soon. What you are talking about isnt exactly that and if theres no KYC or SSN involved you might be ok for tax (for now)...it seems like it might be too far out there for me to trust it with bigger amounts. I'd also think eventually they regulate and shut down any non KYC source for stuff like you're talking about. I'm not into shitcoinery of any kind, but if you can make bank with it, go for it I guess. There's certainly risk there though
 

JeffSTL

OT Supporter
Aug 26, 2004
16,524
Illinois
exactly. but as I stated, those inflows/outflows do not come close to accounting for my actual gains. It's all almost all occurred outside of the boundaries of the exchange.
Exchange all your shitcoin gains into BTC, then move the BTC onto a cold wallet and never fucking sell it
 

Soren

OT Supporter
Oct 9, 2002
36,738
exactly. but as I stated, those inflows/outflows do not come close to accounting for my actual gains. It's all almost all occurred outside of the boundaries of the exchange.

Indeed there are advantages to that approach.
 

Hisma

OT Supporter
Apr 2, 2006
59,213
Reno, NV
Sure. So you can avoid getting taxed when exchanging coins for other coins, but the withdrawal event will be flagged
correct. Right now building a war chest since I recently quit my job. But eventually my profit taking will just be a conversion to a stablecoin that sits inside my wallet earning yield. I only need to withdraw to maintain expenses/take care of purchases. Those withdrawls I will report as income.
 

Menger

OT Supporter
Nov 23, 2011
23,751
exactly. but as I stated, those inflows/outflows do not come close to accounting for my actual gains. It's all almost all occurred outside of the boundaries of the exchange.
so like .... unrealized capital gains?
 

Soren

OT Supporter
Oct 9, 2002
36,738
correct. Right now building a war chest since I recently quit my job. But eventually my profit taking will just be a conversion to a stablecoin that sits inside my wallet earning yield. I only need to withdraw to maintain expenses/take care of purchases. Those withdrawls I will report as income.

Makes sense. But what if you make millions and want to spend like a millionaire? Taxed now, taxed on withdrawal... Either way you get taxed, no? Tax bracket might differ until you start withdrawing 400k+ annually, then doesn't really matter much.
 

Hisma

OT Supporter
Apr 2, 2006
59,213
Reno, NV
No not at all. The only crypto I have interest in is buying and holding Bitcoin. They are gonna regulate the motherfuck out of stable coins soon. What you are talking about isnt exactly that and if theres no KYC or SSN involved you might be ok for tax (for now)...it seems like it might be too far out there for me to trust it with bigger amounts. I'd also think eventually they regulate and shut down any non KYC source for stuff like you're talking about. I'm not into shitcoinery of any kind, but if you can make bank with it, go for it I guess. There's certainly risk there though
yeah I mean it depends how big this stuff gets for me. I don't need to live like a baller. I'm cool maintaining the lifestyle I have now and just controlling the outflows & paying taxes on that alone. The non KYC stuff will not get shut down completely, but they may definitely become illegal in the US. Again it's all the wild west right now as its all so new. And probably 95+% of crypto holders are using KYC platforms where none of what I'm talking about even really applies.
 

Hisma

OT Supporter
Apr 2, 2006
59,213
Reno, NV
so like .... unrealized capital gains?
sort of but not exactly. I can sell my crypto and "realize" my gains by converting it to a stable coin like USDC, but keeping it on chain. So at that point the profit is locked in, but not reported as such as it won't hit the exchange until I transfer it to my bank account. I can hold that USDC in a wallet as long as I want and only draw from it as needed. While also earning yield as there's platforms that offer very nice APYs for parking your stables there. Similar to what coinbase is trying to implement & having huge govt resistance. That staking/lending is already available on-chain, for much better returns than what coinbase was looking to offering.
This is my crypto goal. Eventually move from risky shit to stables, but keeping it all in a wallet earning yield, only drawing from it as needed.
 

Hisma

OT Supporter
Apr 2, 2006
59,213
Reno, NV
Makes sense. But what if you make millions and want to spend like a millionaire? Taxed now, taxed on withdrawal... Either way you get taxed, no? Tax bracket might differ until you start withdrawing 400k+ annually, then doesn't really matter much.
yeah, see my previous response. other than major purchases like buying a house etc, I don't see any need to draw any more than 100kish per year... happy w/ my lifestyle as-is. Also I will likely re-enter the workforce and pay normal taxes on all that, but for now I'm chillin.
I mean this is my whole reason for opening a business but crypto is so volatile and fast-moving, who knows. I could also lose everything via a hack/crypto crash/whatever. But for now, what I've been talking about is possible, and I talk with others daily living this way, ie wallet w/ 100ks/millions in stables, just drawing as needed. Some go as far as to avoid taxes entirely by washing their gains through foreign banks/tumblers. It's pretty wild.
 

Soren

OT Supporter
Oct 9, 2002
36,738
yeah, see my previous response. other than major purchases like buying a house etc, I don't see any need to draw any more than 100kish per year... happy w/ my lifestyle as-is. Also I will likely re-enter the workforce and pay normal taxes on all that, but for now I'm chillin.
I mean this is my whole reason for opening a business but crypto is so volatile and fast-moving, who knows. I could also lose everything via a hack/crypto crash/whatever. But for now, what I've been talking about is possible, and I talk with others daily living this way, ie wallet w/ 100ks/millions in stables, just drawing as needed. Some go as far as to avoid taxes entirely by washing their gains through foreign banks/tumblers. It's pretty wild.

The tax issues made me hesitate to invest big money into crypto but definitely seems like there are some neat tricks available. Good to see you fire-ing off your gains already.
 
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JeffSTL

OT Supporter
Aug 26, 2004
16,524
Illinois
fuck my fucking ass

I've booked 2 round trip flights a couple months ago

I've had I think 7 flight changes on those 4 flights. All of them except one have made me arrive later and leave earlier which I hate. Had one last weekend that changed, and I was able to swap it for an earlier flight which worked out positively for once. Well I just got a notification that the early flight was now canceled and I got moved back to the late flight they moved me to last week :mad::mad::rofl2:
 

AndyP

OT Supporter
Jun 17, 2004
18,396
Sure. So you can avoid getting taxed when exchanging coins for other coins, but the withdrawal event will be flagged
And then they can look back on chain to see the transactions made from addresses that deposit to your exchange address. It’s really not that difficult to follow back. I think its a terrible idea to try and fuck with your taxes on crypto.
 

Hisma

OT Supporter
Apr 2, 2006
59,213
Reno, NV
And then they can look back on chain to see the transactions made from addresses that deposit to your exchange address. It’s really not that difficult to follow back. I think its a terrible idea to try and fuck with your taxes on crypto.
I would bet the only people that would receive this sort of special attention are those trying to dodge taxes and under some major audit.
I haven't explored this software yet, but I've heard of it, so I'm curious to see how it works. If I see evidence that the irs is regularly tracking wallets on chain and and makes people pay capital gains on them on more than just rare cases, I'll eat my words.
Otherwise, I have plenty of first hand knowledge from folks that are living "on chain" and avoiding taxes completely. I'm trying to play by the rules by only treating my achs as realized profits.

Anyway, this is all way off topic. Crypto is a tax nightmare and the government is scrambling to catch up. Eventually it will. But for now, it's still largely the wild west.
 

AndyP

OT Supporter
Jun 17, 2004
18,396
I would bet the only people that would receive this sort of special attention are those trying to dodge taxes and under some major audit.
I haven't explored this software yet, but I've heard of it, so I'm curious to see how it works. If I see evidence that the irs is regularly tracking wallets on chain and and makes people pay capital gains on them on more than just rare cases, I'll eat my words.
Otherwise, I have plenty of first hand knowledge from folks that are living "on chain" and avoiding taxes completely. I'm trying to play by the rules by only treating my achs as realized profits.

Anyway, this is all way off topic. Crypto is a tax nightmare and the government is scrambling to catch up. Eventually it will. But for now, it's still largely the wild west.
Agree for now. The problem is that this can all be used retrospectively if they roll it out in the future. The statute of limitations for tax fraud isn’t short.
 

Sailor Jerry

Well-Known Member
Nov 13, 2007
36,311
Dirtona Beach
I've gotten the CSP 100k, the Amex Gold 75k, and the Citi Custom Cash 20k in the past few months.

Kinda want the Citi Premier 80k, but it seems like you need zero inquiries in six months for that one.
 

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