I'm surprised that the Islanders trade talk is all only focused on 12OV. They have 2 2nd rounders both relatively high. IMO their 1sts are a little too valuable to move for Grubauer. But both 2nds could be a decent base. This would give the Caps 4 picks in the top 46- one of which would probably be used as currency to move Orpik's contract.
The Islanders are able to add a goalie at a decent price to show JT they are looking to win now, as well as keep their 2 1sts. One could then be moved for a top 4 defenceman like it's been addressed in this thread, or just stockpile the cupboard with 2 decent prospects.
Technically Grubauer doesn't have to be moved, but with all the older UFA goalies on the market this year, who could easily take a 1 year deal to go to the team in the SCF, it would be smart for the Caps to do so. If they don't it probably means they are letting Carlson walk. That is poor asset management when you have Holtby already and eventually Samsonov. Additionally, with how well Kempny has played beside Carlson it would be smart to open up cap space by moving Grubauer and Orpik to be able to lock in Wilson, Carlson and Kempny.
Vancouver could be of help too in a 3 way scenario:
Washington in: Calgary and Islanders 2nd
Washington out: Grubauer, Orpik, Florida 2nd
Islanders in: Grubauer, Tanev + ____ from Vancouver
Islanders out: 12OV, Calgary and Islanders 2nds
Canucks in: 12OV, Florida 2nd, Orpik (pure cap dump unless NYI want him at 50% retention)
Canucks out: Tanev + ____?