After spending hours and hours and hours photographing the board, editing PDF character sheets, and writing up power lists on nentir_vale, I can conclusively state the following:
D&D 4e was not meant to be played online, unless you have a D&D Insider subscription and use the online tools. Especially the virtual tabletop, which doesn't exist.
Pathfinder's much easier to GM online, partly because combat does not last all day or require a game board, and partly because all the stuff that you need you can link to directly online.
D&D 5e looks like it'll be closer to Pathfinder, but its "Basic D&D" rules are a gods-damned PDF, and are far from comprehensive.
If we ever get up the energy to do another online RPG campaign, it will probably be Pathfinder.