Specific questions I have is how much $$$$$ do u start with.
Depends upon the size of your rosters but the standard for a 23-man squad is $260 or approximately $11 per player. If your rosters are bigger than that, I'd add about $5 per man; it's not proportionate but the bottom of the barrel guys are going to go for pretty cheap.
How do you figure the amount of years a contract is worth.
I don't do contracts: personally I hate them. They're arbitrary; they make all sorts of complications as to keeping vs. cutting and dead salary cap and just turn everything messy. It's much better to just have increasing salary bumps so that the owners can eventually decide when a player is too expensive. I use increases of $3 the first year, another $5 the second, and $10 every year thereafter and it seems to work out just fine.
What order do you go in to do the auction #1 ranked goes first or shitty guys first.
There's a number of strategies on this... personally I think it doesn't matter oh so much. But if you can save some $$ and hold off nominating someone who everyone else is missing, it can work out for you.
How does free agency work.
There's two main systems. The first uses a FAAB (Free Agent Acquisition Budget) where players bid on free agents every week and then whatever they're purchased for becomes their salary. The second just uses a normal waiver process which is easier but not quite as interesting. We do it the second way and then stipulate that all players gotten off of the waiver wire have a keeper value of $8 so as to reward getting people in the draft vs. just picking up the breakout guy.
0-3 to 4-3. Worst choke in the history of baseball. Enough said.