2026-27 is only 3 years away, a couple years after that is only 5 years away. Doing a full rebuild in 5 years requires drafting a couple franchise players and then have good players want to sign with you to supplement your draft picks. A full rebuild in the NHL's least desirable market will be painful and require a lot of luck. Odds wise we are probably much more likely to miss the playoffs for a decade or more then we are to be competitive in 5-7 years.
24 season, 25, 26, 27, = 4, plus 2 more? 6 You specified that that would be with all of the best case scenarios working out. That would mean drafting a couple of franchise players, among other things.
I don't believe it is ever necessary to have high end FAs sign with you to supplement your picks. We do alright signing the low to mid level ones that may be needed.
The Jets have a choice between 2 quite different timelines. There is the one where they let everybody walk after trying to get another PO run out of them and there is the one where they jump start the process.
Trading all of Dubois, Scheifele and Hellebuyck should yield a very good start on a rebuild. Draft about 17-18 this year and bottom 5 for a couple after that. Add those assets to the prospects we have now, McGroarty, Lucius, Lambert, Heinola, Chisholm, Gawanke, Salomonsson, Zhilkin, Divincentiis, plus a few lesser ones who might yield 2-3 more NHL'ers. That is an already well started rebuild. We still have JMo, KFC and Ehlers plus a couple of middle 6'ers and a few bottom 6'ers.
We might be a little too young, lacking experience and leadership. That can be dealt with through FA and/or trade.
Goal will be the hardest spot to fill. We have a few prospects but no blue chippers. We might not even get a good backup out of the bunch.
A lot of teams have started their rebuilds with a lot less and it has taken them a very long time. A misstep or two can add years to the rebuild. There is no guarantee on the timeline. But with a good start it doesn't need to take a decade or more.
Edit: I meant to point out the money saving too. The idea is that Chipman wants POs this year to recoup some of the losses due to Covid. Jets could be shaving 15 mil or more from the expense side for a year or two. That makes up for some lost ticket sales.