You are the keen one!
Why trouble your friend to change anything, particularly if he is used to Aol..... Aol may not be your way but it is his, and if you are physically no closer than email it is probably better to let him go the way he knows.
My crystal ball shows me that to transfer ALL the stuff he wants to an unfamiliar environment is unlikely to win you many Brownie points. Aol is very Nannyish and very stable. Once used to Aol there is no need to change.
A friend of mine, who supports software for major firms, finds it easier to use Pipex for the sort of delving into critical files and sending data both ways over the net. Aol (quite properly, tries too hard to prevent my friend having control over a distant server!)