After looking through the different teams, I thought the best challenge for me being a newbie would be trying to take control of the Maple Leafs and rebuild them back into being a Stanley Cup Contender. I am also using my Flames in another game, but for the posters on TBL, the Leafs game will likely be the more entertaining. I am also using the unfaking database and the patch.
So I started and already found myself in salary cap hell with some really stupid contracts (thanks Ferguson), some bad scouts, and some poor assistants. I canned Ladoceur and hired Paul Coffey as an assistant coach. I basically hired a brand new scouting staff and hired Charlie Hodge as an assistant GM - high scout type ratings.
Looking at the team, I could not justify paying Bryan McCabe 7.1 million a season for 5 years so I traded him and a scrub to the Lightning for Brad Richards

Richards is 26 and making lots, but he's a much better investment than overrated McCabe. I then traded Tellquvist to the Sharks for a 3rd round pick and sent Belak down to clear some cap room. I still have some issues with the cap because of Kubina, Gill, Peca, and Sundin, but I'll likely keep them all with the exception of Gill - who I am trying to unload.
More updates when I make some deals, but there's a lot of work to be done to rebuild this team with a nice blend of young players and players in their mid-20's.