Like Tarmogoyf in Modern, Wasteland deserves several reprintings. And like the Fetchlands and the Shocklands in Modern, the ABU lands need to be kept affordable. Finally, the Cryptic Command of Legacy is Force of Will, and should also be in the 'reprint every two years' list.
Yes, Vintage Masters already made many Legacy staples less expensive, but there is clearly a lot more room to decrease the high price of many of the format staples.
There is, however, another route, and one that could potentially generate more sales for Wizards, and that is to remaster each block as was done for Tempest. That would work, especially if the next one is Mercadian Masques, but that would mean a much slower schedule to get new players to have a nice Legacy staples stash to play multiple tier 1 decks. In my opinion, the only way for a Legacy online set to be as successful as Vintage Masters is to do as VMA did: 'do it once, do it right,' and the only way to do that is by issuing Legacy Masters Summer 2016 with 'all the trimmings.'