Welcome to FT!
I can't say I've had the same experiences, but will offer my thoughts...
- While I do sometimes look at what's available and then plan travel from there, it's because I have such a wide range of travel desires that it's never a negative for me. So with that being the case for you, would the old "pros and cons list" approach help wrap your head around choosing to pay cash in those situations? Or you could post here when confronted with such a choice - occasionally folks will post a "help me decide whether to redeem miles or pay cash" for a particular flight scenario, which usually results in a number of people weighing in with their opinions/recommendations.
- Amex has a great range of available transfer partners. How well do you know the Amex transfer partners' programs in terms of what shows up as available on their websites, and alternative places to search for availability? Some people aren't aware that with some FFPs, not all partner awards show up online and you may have to call to book; also there may be other partner FFP sites where you can search availability first before calling.
- The Award Nexus site is an excellent tool for searching award availability. You can log in with your FlyerTalk login to search for free:
https://awardnexus.com/user/login?url=%2F
- As you may know, award availability is very fluid and can come and go quickly. ExpertFlyer is a useful subscription site where, among other useful tools, you can set award seat availability alerts for many airlines. This can let you get a jump on openings much faster.
https://www.expertflyer.com/
- While I personally don't use them and don't think they are needed for the vast majority of people, you can use an award booking service, which for a fee will look for and book awards for you. It might be what you need if you're not finding any pleasure in spending hours searching (I happen to enjoy doing it but not everyone does!). There's a thread on here about those services including reviews:
Award booking services - a list and some reviews
- You could also look at other redemption options for the miles & points, besides flights and hotels. While the other options often aren't the best value for most people, given your situation it may be something you would like and feel better about doing...special events, experiences, products, services. One unqieu, high-end example:
https://frequentmiler.boardingarea.c...million-miles/ Points and miles can often be donated to charity, as well.
Good luck and have fun whatever you do!