Interesting thread. When I first started SP's I was in my early 40's and I was fairly nervous. Ended up meeting Totally Touchable Tiffany as my first SP experience and it completely changed my view of things. For starters I expected an SP to basically go through the motions with an average looking older guy like me, but that's not what happened, I was made to feel very special and for that I'm grateful.
Over the years, maybe because of age, maybe because of $$, maybe because of who knows, I gained a lot of confidence and found that as that increased, younger women (ie in their 20's) seemed to smile at me more, perhaps because I unknowingly initiated eye contact, and now I pretty much think that an attractive woman, is just another woman, albeit with a little special something going for her.
Also over the years, I got into the Sugar Daddy role with one young women, who was 24 when we met and it now 29. At first I probably fawned over her too much because it was an awesome situation, but over the years, I've come to few her as partly a daughter, partly a friend, and just someone I enjoy helping. In some ways I think that since I only have one child to support, I can help her and her daughter out and it's like having a friend with benefits situation.
So back to the OP's original comments as to whether or not people think they're good enough for hot chicks, part of it is reality, (ie if your 50lb over weight, you probably aren't) and part of it is simply psychological. If you're not far off from average looking, then treat them the same as anyone else and they'll likely do the same back to you. Put them on a pedistal and often as not they'll feel uncomfortable and they'll view you as not strong. If you're asking them out try not to worry too much about what the answer is, make it a group thing or coffee or something that's kind of neutral on the relationship scale. I believe that woman like strong men, if not physically then they at least like to feel that a man can look after them financially, have decent social skills and treat them and others around them with respect.