If Michael's desire to go legit was true, than this point in his life would be a better time than ever. But now that i think about things come to mind that would delay going legit. Like you said he has a big family to care for and the legit business world is frankly something Michael had never been a part of, so he would have to atleast go after one big svore to have enough money until he found a legit money source. Everyone knows though that one score leads to another and another. Most might think that Vages was a legit money source but unless you had muscle to back your business up than you would be pushed out of town quickly. I beliee that by this point though Michael had decided this was his destiny, because if he wanted to leave the life at this point who would stop him??????