Check the conditions here: http://desowv.org/trail-conditions
The THs at Wrights Lake(Rockbound and Twin Lakes TH) are good starting points, but if you're only going for a couple of days and want to get into the heart of the scenerey, then I would recommend entering from one of the East side THs (e.g. Glen Alpine, Bayview). Really though, Desolation is relatively small, so if you can churn out 15 miles a day then you really can't go wrong. The landscapes also offers great opportunities for off-trail travel with some pretty good visibile landmarks.
Check conditions on the volunteers website, give the local Ranger a call, and plan accordingly. If it was me and conditions allowed, I'd go for Glen Alpine TH to zone 28 (Half Moon Lake) for night one. From there, you're right in the middle if you choose to explore south towards Aloha, or north towards Velma.
Have fun and be safe!