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I personally would avoid airline/hotel specific cards, although of course everyone's situation varies. You'd have to value the free checked bags, Admirals Club access, and opportunity cost of using that spend elsewhere pretty heavily to justify the AA card imo. For a $595 AF, I'd rather get the CSR which is $550 but comes with various credits and gives UR points, which are flexible and not locked into AA.
Chase ecosystem is miles better than Cap One. VX is a great starter card for those new to travel, given its simplicity (2x on everything) and easy fee coverage: $395 AF with $300 travel credit via portal (which many don't like to use, but still) and 10k miles ($100 if 1cpp). Pair it with the no AF Savor One and it's a decent duo. But the transfer partners are severely lacking and they also nerfed the Priority Pass benefits.
Personally I prefer CSR (or CSP if you don't need the premium benefits) just because I value the transfer partners and have the trifecta. If you do want a Chase card at all, start with that one because they're the most stringent given their 5/24 restriction. Easier to open a CSP/CSR first and then get other travel cards later than the other way around. Happy to answer any questions via DM if you want more details or have more personal info you'd rather not post.
The best cheapo AA card is the red one from Barclays, they give out brochures onboard with very good points bonus. Compare it to the signup points from the cheapest Citi AA card. Both will be under $100/yr and give you free luggage and a slight boarding group upgrade.
Has anybody ever used the Hilton American Express for travel points? I believe this has a $95 annual fee?
Hilton points are pretty bad for the reasons you mentioned. You can often buy their points at a big discount, so I see no reason to get a card that forces you to earn Hilton points.