It will be a while before I ever move up to DIA but I was wondering if I can just stay a while at my DII team and skip DIAA. Is this possible? If so how long do you suppose it will take?

Nope, gotta take the steps 1 by 1.   Just a FYI.  It takes about 85 wins to get to DIA so stay in DII until you hit 80 wins and then grab a DIAA team that can win you 5-8 games and then move onto DIA after 1 season at DIAA.   (you can move to DIAA after about 45 wins but it sounds like you like DII and want to stay there as long as possible)

Yeah I need to learn more about the game before I make the jump so I I'll be in DID for a while