Thank you, Carmel!
I actually find that men are much more one-dimensional when it comes to relationships. If she's attractive, she's in like Flynn. Women are more attracted to nuances. It's chemistry. And humor. I have found myself insanely attracted to not so hot men (no, money wasn't it either) and not remotely attracted to the hottest. In fact, one guy, who was hot, rich, and nice wanted to marry me. I just couldn't get it up for him. My friends thought I was nuts! But you can't fake it. Well, I can't.
So, it's not necessarily looks or money, honey.
I will say that I agree with Atomic's assertion that women will appreciate you more in a few years. One of my best guys friends--who is the best guy I know--was not appreciated until his late mid twenties. (I was eight years older and his sister's best friend, so it was a "no fly zone" to his chagrin. Not the age--he was always more mature than most.) Now women are all over him, and he found someone equally deserving. (Thank God! I put her through a hell of an interrogation!)
Those MILFs you mentioned? I can tell you from my own perspective, of having a really hot and nice younger guy attracted to me that it is great for the ego, but women usually value maturity. it's hard to conjure up attraction to someone who is really unseasoned, even if you think he's great. (Having a job, understanding ups and downs of life, experiencing loss etc.)
The MILF who was insecure? It might be because a young man might not appeciate her body so much as you would the more "perfect" college figure. Maybe that played a role. I don't know. I do know that I have a greater appreciation for my body at 36 (it's still damn good!) then I did when I was a size 4 at 22.
incidentally, when you do recover from your drought? Remember this: If you ever want truly mindblowing sex, with whatever woman at any age or size, all you have to do is treat her like she is the hottest thing since Betty Page, and you will be amazed at its disinhibiting effect. If we know that you appreciate, adore, salivate over, hunger for, and generally feel that the very touch/taste/and feel of our skin is the heighth of your pleasure, we are pretty much putty in your hands. If we see that in your face, we won't pull that lame, bullshit too inhibited and insecure with our bodies crap that we sometimes do that does nothing but ruin a unrestrained, good time for all.
Hope that helps! In any event, good times are ahead, Red!