I would like to position myself to be an "in demand" 50 yr old male. I am not a swinging single or trying to pick up young girls. I prefer a classy mature woman within my age range. I have several college degrees, I work out in the gym, look attractive, modest income, look young for my age, and dress stylish. It seems like the only way a 50 yr old can be hot is to be super wealthy... lol.
Young guys don't need money. I can attest to that. For example, a young guy can be poor, single, drive a beater car, dress cool, be somewhat attractive, have inner game and be wanted by MANY women.
The game changes after age 40. I am thinking of getting off social media, going to wine tastings or conference events and more appropriate settings.
I'm 50 divorced with kids, yea I have money, but I am far from rich. I never have problems getting dates, and getting women interested. Like you I work out a lot, which helps, but I think you get that it's probably the places you are going that is the problem.
By the time you hit your mid-30s, women stop giving you extra-credit for 'potential', and start grading you on who you are. So you are right, past 40 it really isn't a game anymore it is who you REALLY are. If you really don't have anything going in life then yea... you are going to have problems. Here is how I meet women:
Yoga: I'm shocked that more men do not take this up. Especially someone like you, just starting out, you have built in rapport and need 'help'. The studio I practice at has get togethers first Friday of every month. Always fun.
Chamber of Commerce Networking Events: Seriously, start a business. What ever it is that you want to do, it can even be a part time thing. SBA has free counseling and they can get you started. Being an entrepreneur is interesting, and you have built in rapport with chicks at the network events.
Get involved with charities: I'm on the board of three, and there is often plenty of opportunities to meet women.
I also do wine tasting and anything else that looks remotely interesting. My source of interesting stuff to do is Facebook under local 'events' where I live there is seldom NOTHING going on. If you are in a place with ZERO happening, and you are not happy, then go ahead and move.... you don't have any reason to stay where you are.