On a realistic note - with my mouth in its current condition how likely am I really to be able to pull anything off anyway?
I know you have your concerns about how to go about approaching women, and others here have given you great advice on that. But, this is your real sticking point. Because even if you can manage to repeatedly be courageous and make headway with a particular woman, you may be stopped mentally and emotionally by this dental issue.
What exactly are you worried about? The woman judging you, being turned off, kissing, etc.? If a woman is going to be turned off by you, then you don't need her anyway and she's definitely not for you. And if she is going to judge you unfairly then the same goes, you don't need a woman like that.
There are some women who are not going to be into kissing, so you wouldn't have to be too concerned with that. However, I don't know how many women are like me in that area. Perhaps some other women could give their opinion.
Dentures would help your confidence by leaps and bounds I imagine. Is it absolutely impossible for you to wear them? Have you tried it out and it failed?