Doesn't even take 30 wins... here's the Romero breakdown for those who moved up to DI-AA:
Kyle128084: 28 total wins, 24 D-II wins (and had to have taken a loyalty/rep beating for a lateral DII move in season 3)
kas1007: 42 total wins, 30 D-II wins, 1 NC
ulrich: 39 total wins, 26 D-II wins
mannowar (me): 46 total wins, 32 D-II wins, 1 NC
Maybe it does have something to do with D-II wins and apparently nothing to do with overall wins or loyalty/rep. No knock on Kyle here, just not sure what qualified him. Heck, I had 28 wins after season 2 and more than double the playoff wins... and, I didn't have the rep/loyalty loss for a lateral move and didn't qualify.
None of this really matters all that much, but once again, as in prior versions of this game, we find this big grey area that no one really seems to absolutely KNOW what's going on.