I hate the playing to lose mentality, coaches and GMs should always play to win. Tanking is a bad idea, it hasn't been proven that it works in the NHL anyway. I am against trading young assets or draft picks for vets to win now.
We should always keep our first and second round picks, we shouldn't trade them. The game is also getting younger and younger while the CBA way under pays ELCs, under pays RFAs, and over pays UFAs. We need to sign more ELCs, some RFAs and stay away from expensive UFAs. Only sign a UFA on a short term deal, 2 years max, less than $4 mill a year. Chayka killed us with the draft pick trades and penalties.
We have 2 over paid players with NTC/NMCs, OEL/Kessel. This is where the mistakes are made that kill your cap. We need to stay away from these types of deals, it kills our flexibility. An example would be when Chych gets to his UFA deal and wants an 8 year deal at $10 mill+ with an NMC, we should trade him, get some assets but avoid that type of contract. We have nothing but downside. I like Chych, not saying we should trade him at all now, just saying his next contract could be a trap.
If we trade younger good players, we should only do it where we have a surplus. Garland/Keller/Schmaltz come to mind, all similar smallish players. I would consider trading one of them if we can get a potential top 4D, maybe a first round pick, or larger winger that we don't have, some combination, change the mix.
Bottom line, lets take advantage of the CBA structure, sign ELC/RFA deals, less risk with more flexibility, and stay away from expensive UFAs/term/NTC contracts. The team has more upside and less downside with ELC/RFA deals and we take 90% of the risk in UFA/NMC/long term deals.