You're not a bad looking guy, no reason to ever be shy. I second getting help from a qualified physician, maybe just a therapist before then. Just need to make a change and come out of your shell, this life is meant to be lived don't spend it in the shadows anymore! You got this!
I've had some of these issues in pass. I find gym helps with self-esteem and meeting women. Get gym membership to one you feel comfortable with at first. Maybe knot most popular one. Move later if you want. Over time you'll improve an so will your issues. Small talk with ladies, knot like hound dog , casual over time. Focus on gym part mainly. That's how I picked up my women of 12 years. An one before that. I would definitely get that low testosterone addressed.
A doctor will more than likely prescribe an SSRI or something similar, which in turn will kill your libido and drive to chase women. Not that that is necessarily a bad thing, but you say you want to get laid.
Being in Vegas you have never once thought of just hiring an escort and letting her handle everything just to ease your anxiety a little so when you are actually with a girl you like your anxiety will be lessened.
I'm not sure all the details to your situation and you may very well need professional help, I'm just very leary of psych drugs or anything those docs tend to prescribe.
As stated previously, I would get your hormones checked and get with an endo first and fore most and see how you feel after some possible treatment, if that's something you would be a good candidate for.
Edit: Judging by your pic you just look like an average dude, not sure why you are feeling so insecure about yourself.
I enjoy a comedy club or live concert, just go for you and if you see someone interesting go say something to them in passing...ex. Go to get a drink and on the way make eye contact ask the ladies as a group if they are having a good time...go to the bar and get your drink and observe for any signs of interest. If you throw enough bait eventually you will get a bite and even a catch, without going in for the kill you eliminate rejection, and you save time and money as some men get set up to buy drink for the night by players.