You're right.. We'll hate the deal if the Leafs bow out again in round 1 .. probably dislike it if it's round 2 ... etc.
For the failures of the core I'm skeptical that ROR is going to turn them into a Cup running squad, so to me dealing the picks could leave them in a tough spot. If you believe in the team, this clearly fits a big need.
But another playoff failure could mean bigger changes and the Leafs have the assets to recoup some picks at least. So there's that at least.
It's great they didn't deal any of their prospects that could make an impact as earlier as next season. They need the ELC value.