What the OP should do is try craigslist or some dating site and try his luck with what he is looking for that way.
Or he should just go hang out at the Chic 'n Deli and pick up some Cougars.
But thinking he is going to get a discount because of his looks... What a joke. Don't you think if these girls wanted to spend time with a good looking guy they would have no trouble finding one on their own?
I'm by no means rich (yet, here's hoping), I'm over 30 and just an average looking guy. A bit chubby, etc. but not a bad looking guy. I used to have a girl I would link up with similar to what the OP was looking for... I met her on backpage... I'd buy her stuff for her kid, toss her a hundred or two here and there and we would hit it. Lasted a few months.
In the end I found I liked going to a SP better; I got a lot more out of the time and the quality is so much better. If you want a "fake" girlfriend or a mistress it's going to cost you, big time. If you just want an hour or two of blissful indulgence, see an SP and don't cheap out.
If you want more GF time then you are simply going to have to get a GF. If you are as good looking, etc. as you seem to think finding one shouldn't be that hard. Okcupid and POF are free, go search casual sex or whatever.
Good luck.