Gotta play the role right Rail. Sure a lot of people will try to overcharge, but not all. Just be dressed out like a serious Sox fan, maybe a New York Sucks shirt will do it well. Look a die-hard fan and you will find someone that isn't out to take you for 30% more. If someone says yeah, I got a ticket, 2 grand, just laugh at him. He is a guy looking to get lucky, that is his price for getting him to give up going inside. In any event if you want to know the going rate on a ticket just hang out about 2 hours ahead and ask. If you don't see many tickets out there, you could be screwed. Once again set your price in your mind and don't go over it. If $500 is your price, put that much in your pocket and a few bucks for walking around money and that is it. When someone asks for more, just say hey this is all I got. Worst thing is he says no and you just go back to work. Hang out at a local bar for awhile if the prices aren't to your level and go back out after a bit and see if anything else has hit the market.
Accept the fact that your chances of getting in aren't 100% before you get there and then you won't be too disappointed or pay way too much.
I made it to a Superbowl, a Final Four, 3 Rose Bowls, a NBA Final game, Kentucky Derby, US Open golf and tennis...I could go on and on, all before I turned 21 by buying outside the stadium. The key to doing well on the buying side is to set a price, but expect the worst. Toughest tickets I ever had to deal for were games no one would remember. There just weren't tix out there and I just said forget it and skipped the game. Those are tough to be sellers for and even worse to be a buyer. The market ain't perfect, that is for sure.