Trading Ovechkin isn't going to happen. No established contender can fit the entirety of his $9.5M contract. The bottom feeder won't be able to afford him. The Caps would either have to retain a significant portion of the salary or take a sizeable cap dump in return. Having $4M+ in dead hit cap on your roster for 4 more years is something you do in a long rebuild, not a quick one. You can't retool if you trade Ovechkin, it signals a lengthy and comprehensive rebuild.
The only possible exception to this I could see would be Buffalo.
Similarly the cupboard is stripped down in terms of picks and prospects. They don't have a pick until the 4th round this year. They are missing 2nd round picks for the rest of eternity. The prospect pool is thin and mostly loaded with fringe players. Even some of their nicer looking late round picks (Gerisch, Pinho) aren't guaranteed to sign. The Shattenkirk, Eller, Laich, and Glenncross trades have helped to leave the system barren.
Without a stocked farm system or at least draft picks to refill it, gutting the team and rebuilding from scratch is a tough sell. There's little hope for a quick turnaround when you don't already have youth you can turn to carry the torch. Madison Bowey and Jakub Vrana aren't going to carry this team to the promised land.
The only realistic path before the Capitals is to take a step or two back and attempt to retool. They won't be "the Cup favorite" the next couple years, but they won't be completely rebuilding, either. It's going to be a transitional period, but they're going to aim to try and restock and turn the system around in a short term fashion, largely around the same core players.