The more I hear about your story, the more I think that I feel something sounds sad. You should be killing it in the dating market and yet you are content to, by our own admission, settle for a paid hook-up with a 60 year old hor and it honestly sounds like they probably love dealing with you as a client and taking your money, and you are probably the icing on their cake as far as their occupation is concerned. However, its still not right for you as you can get better women, in both looks and quality for free if you worked on the social awkwardness.I've been told I'm an 8 and a half out of 10 on the looks scale.
In my experience, when I've chatted with girls on dating sites, they're initially intrigued by my looks. Then in many cases, they quickly end up losing interest because of my social awkwardness.
You DMed me some stories of civvie conquests and I'm floored. You have great potential. Why not work on your social awkardness with paid hot women and focus on more paid dinner dates or outings that involve you opening up and talking. I'm not sure how much that would cost, but there are escorts that provide that type of service with getting laid as part of the package. I think just having a couple of hours rendezvous per month with escorts that are below your SMV is not doing you favours at this stage in the game and you should budget for a more comprehensive 4 hour date that includes dinner, conversation and the sex afterwards. It may cost more money, but I think it will be more helpful than just getting your rocks off with sub-par women in the first place.