I'm meh on Hilton as their points arent worth shit and they dont partner with Chase, but thats me
You are probably shorting yourself a ton of points if you arent looking where you're spending the most money and seeing if you can get a higher earn rate than 1.5 a CFU or CIU gives you, a CSR is only 1 as you said.
As far as maximizing points, its all about transferring points and travel partners. I dont have a ton of experience there but there are Facebook groups and sites that help a ton. I think awardhacker.com is a popular site to look up. For example when I was booking a trip to Alaska, I had a ton of chase points. I transferred a bunch to Singapore Airlines because one of their partner airlines was Alaska Airlines. With the Singapore miles I booked roundtrip tickets on Alaska. I ended up getting several cents per point that way. Sadly Covid canceled the trip and I have 75k Singapore miles just sitting there that are going to expire in like a year or two I have to make sure I use and dont forget about