Your post was massively helpful mate - once it's put into simplistic terms 'put up or shut up' it brings things into perspective. Since you've said that, I've tried relating this to other areas of my life:
Learning to drive, starting a new job - you're always going to be out of your comfort zone and, inevitably, mistakes are going to happen! The sacrifice now will be worth it later on
Interesting point on your dislike of gaming with mates though. Although I'd worry my friends would take the piss, I'd far rather that than be the creepy guy who's crawling bars on his own!
Like you said though, we wont see 99% of these people again so who gives a fuck!