Tinder is murder. I'm 39, male, tall, attractive, fit, educated, etc. in a small-midsized city and it's extremely, extremely, rare to get a match. Very occasionally (1-2x/year, in my experience) things progress to a date/hookup. If you really want to use apps, I'd suggest exploring others. I've had the most success (relatively) with Hinge.
I'd agree with sibling comment that meeting people out in the world can be a lot more fulfilling. You probably know within seconds if you're (physically) attracted to people in the world. Apps can be deceiving.
Keep in mind that in your list of five items, you can manage all of them. If you want it badly enough, you can change #2, and based on your comment I'd argue this (negative self-image) may be at the root here. #3 is not a problem if you don't let it be--plenty of Bic-ed bald guys with attractive mates out there. We are all doled the genes we must live with, but I bet many of the perceived issues with #1 and #3 will improve if you fix #2. None of the women I have dated have cared, at all, about the money I do or don't have (#5). I live in a backyard cottage. I drive a 20 year old car. And as for #4, I can tell you I had a no-strings-attached relationship with a 21 year old for several months last year. She worked at the farmers market, which is where we met. I don't mean to brag, but you need know that each of those items in your list really is in your control.
It's a grind and a slog and it's scary to have conversations with complete strangers. But if it's something you want, I tell you it is possible.
EDIT: I should also mention I'm no "natural". I was terrified of girls in high school, didn't kiss anyone until I halfway through college, was stuck in a loveless long-term relationship for a decade after college because I was sure no one else other than this one person would ever love me, etc. It took a lot of learning and healing to describe myself as I did in the first paragraph. If I could do it, you can do it.