The basics you list at the beginning aren't much of a problem for me. I'm not debt-ridden and poor; I am an engineer after all, not a minimum-wage worker. I drive a nice Volvo. I frequently get confused for someone 15 years younger; I'm tall, fit, and I think I dress well enough (nothing fancy, but not baggy crap or anything) and am pretty meticulous about my grooming.
Some women do seem very interested, but I'm just not interested in them as they look like the NASCAR fans hoping to score someone who can give them a set-up.
Once you are interacting, STFU and listen. You can initiate conversations, and steer them, and you should, but you need to be a good listener more than anything else.
Honestly, I am pretty good with conversation when I meet an intelligent woman, and I am very good at listening, and always have been. My problem is getting to this "once you are interacting" point; this has *always* been my problem: actually meeting women I have some kind of interest in, and then getting to that "interacting" point (i.e., a date). My problem has always been a lack of opportunities to meet worthwhile women, probably largely stemming from my career field and also my lack of interest in things like bar-hopping and church-going. (I actually do go to bars once in a while, but nothing ever comes of it; I'm not a drinker (besides a glass of pinot noir maybe), so I just don't really mesh with anyone in the crowd at all.)
Honestly, if I could move to Manhattan, I'd probably do really well there, between the surplus of available women there, and also my cultural tastes (I enjoy things like Baroque music, and don't care at all for things like NASCAR and 4-wheeling). There's probably a good number of attractive women there with similar tastes. whereas where I am now I don't think there's any, despite this being a metro area of 2M population. Unfortunately my career and other factors make moving to Manhattan impossible for me.
I do appreciate the advice (though it's probably a good dissertation for anyone with this STEM background, not just me), and you're the second person in this thread who suggested martial arts.