Hey
Didn't think I'd run into a fellow politics student doing this, if you ever run for office, I may need a job so I'll give you the basics.
You should definitely not wait until your hair grows out, because it matters very little. I appreciate that things that seem unimportant to others can become major hangups to you but listen dude, I have braces with big elastic bands hanging out of the tops to fix up an under bite, and there's no way I could forgo picking- up until that comes out

And obviously, I should point out that Neil Strauss, who may be the world's best pickup artist is totally bald!
I spent too much money when I started this so I'll give you a short overview of the major schools of thought
Indirect Game= Neil Strauss, Mystery Method, Swinggcat
Direct Game = Attract and Date, Mode One
Cocky Comedy = David De Angelo
Neuro Linguistic Programming = Ross Jeffries, October Man Sequence
Natural Game = Zan, Vin Di Carlo, Wayne Elise, TheApproach
Other = Pickup101, BadBoy, Tyler Durden, David Shade, Carlos Xuma
Inner Game = Hypnotica, Steve P
By and large, if anybody else tries to sell you anything, do not buy it because there are a lot of fakers trying to make a buck with theories they have conjured up in their imaginations that havent been tested. That said, the other route is to throw away all your money

As a first step, Google "fast seduction 101" and read through their pickup guide to get a feel for basic ideas. If you want to buy something I recommend mystery's venusian arts handbook which I'll give you for nothing if you want. This is because it can be adopted to fit any other method you can imagine.
As for your other questions try not to get drunk when sarging, having one or two to get rid of nerves is more than enough. Sarging alone is fine, having a wing parter helps in situations like say, when your target is out with one friend and she doesn't want to leave with you because that would mean leaving her friend alone. In that case scenario, your wing can keep the friend busy and that makes your life easier.
Your mental barriers should come down with experience but if you find you're having serious confidence (ie "inner game") issues check out hypnotica's website; he has some cool free downloads and his sphinx of imagination cd is mind-blowing
Have fun in Las Vegas