I think that's always a risk with playoff teams. They often spend (picks / prospects) at the TDL, but end up with a disappointing performance in the playoffs.
The calculation is always related to how strong a contender the team is. If the Jets look like a marginal playoff contender without a clear chance to go far in the playoffs, then the Jets have to be circumspect about planning for the future. The Copp trade is perhaps a demonstration of Chevy's approach. The Jets had a "chance" to make the playoffs, but didn't look like they were going to be a contender. He kept Copp for that season to see how the Jets would pan out, but traded him when the Jets looked "meh".
For next season, on "paper" you could make the argument that the Jets are considerably stronger than last season, and they were a strong team down the stretch last season (7th in the NHL in 5v5 xGF% in the last 30 games), and were on a "heater" going into the playoffs.
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Looking towards next season, if you compare what the Jets have added and subtracted from the roster (since the TDL), the Jets have had a big net gain (in xGAR and xWAR) by swapping PLD, Wheeler, Stenlund and Manalainen for Niederreiter, Vilardi, Iafallo and Namestnikov.
If you add in a healthy Ehlers and Perfetti for the full season, the Jets look quite a bit deeper and stronger than last season.
So, most teams would not be looking towards a rebuild with that quality of roster, but it will be interesting to see how Chevy balances present vs. future value.