A neat thing in Out of the Park Baseball is random debut where you start in any year you want and every year it introduces players from every point in baseball's history. You can start with an inaugural draft too, so you can have Babe Ruth, Nolan Ryan, and Mike Trout on the same team going against Derek Jeter, Mickey Mantle, and Honus Wagner. It can be quite amusing.
This is indeed a great way to play. The game will automatically introduce expansion teams, league realignments, team moves and changes, financial changes, everything. I had a blast starting a league in 1901 once, I think I played until 1918 or something like that.