The route is usually snow packed after the keyhole, so you have no summer "spots" on the rocks to follow you'll need to know where your going. Crampons, ice axe, and avalanche education and knowing how to use all of them.
Then a lucky weather window, 2 am or so start, warm clothes, in top shape, and your ready for the keyhole in winter
IMO, its a big pain in the ass. Deep snow makes for really slow going, and the trough looks like it could be pretty avalanche prone. I'd say that the easiest way up Longs in the winter is the N. face. It is a much shorter, more direct route, and is really only 1 pitch of 5.4. With a little scrambling you can get up and down just fine with 1 60m rope, and only 1 rap.