Oh...I'm sorry - Are there guarantees if Lou keeps doing whatever it is he's doing?
I'd argue there's more of a guarantee that the Isles continue to fade away from Cup contention then if we try a new path. That means not just a new GM, but a total investment into a youth movement that includes elite young talent.
I love every Islander who put on the uniform the last few years and gave us some great memories, but the last thing I want to do is watch (much less pay money to see) aging average talent continue to miss the playoffs...And get nowhere near a top 3 pick.
Here's the problem you're missing...
Both Panthers and Stars' core group of players was/is SO much better than the Isles "core" group. Sure most around here would say our core players are Sorokin, Barzal, Horvat, and Dobson (and yet many want him traded), but compare that to the top 4 players on any contending team and it's a joke how much of a gap there is to even consider this current Isles team close to competing for a Cup
You have to build your core group first...And it needs to be a LOT more talented than what the Isles have. Then you can talk about retooling, but you can't retool if you don't have a foundation. That's why I'd argue the Isles are still "building," and without hitting on a (top) draft pick(s), I don't see how they're going to get that top (young) talent to build there core.
There are no guarantees to anything in anything. All I am saying is that rebuilding is not some magic pill that will make everything better. Whenever you release or trade talent, you get worse. Even if you trade a Kyle Palmieri for a 2nd round pick, you are getting worse. You are trading a bona fide middle 9 player for a lottery ticket. a 2nd round pick has a 25% chance of playing more than 300 games. If you have enough lottery tickets, you may get more Palmieris. My point is that as the number of teams goes up (32 currently), the amount of NHL talent dwindles as well. Furthermore, with the cap going up, there will be less UFAs to sign and trades to be had for salary dump reasons. The sharks and Blackhawks are rebuilding. There appears to be no end in sight.
Rebuilding is a general term that can mean different things. Stripping the team to bare bones and starting from scratch can be painful for a very long time.
To answer your other question, No. I do not believe the way Lou is doing it is correct. His team building strategy is too far the other way. He is afraid to make changes. He signs average players to very long term and refuses to cut bait on players 1 year too early, which is key for sustained success. He takes the above point to an extreme. He is so afraid of the unknown, he overpays for the known and continues to double down on it.
You also point out the Stars as having a better core prior to them being good. Let's take a look.
2019-20 Stars - a very mediocre team and aging (29.4 average age)
Here was their core that year: Seguin, Benn, Heiskanen (20 yo). Their top 2 players were not PPG players either. People thought they were doomed because of how overpaid and slow they looked.
The also had Hintz (23 yo, 33 pts in 60 gp), an aging Radulov (34pts in 60 gp), Pavelski (31 pts in 67), and John Klingberg (32 pts in 58 gp).
The 2021 Stars team wasn't very good either with much of the same core, but you see Jason Robertson introduced.
The following year however, you saw Robertson, Hintz, and Oettinger take a huge step and the team has 98 pts. Ever since then, they've been cultivating their young talent and improving.
The young talent they've amassed are not top picks. Just good scouting and development. Their hit rate for impact players is abnormally high.
So I disagree that they started with a better core but they have done a much better job drafting and developing picks that you didn't have to tank for even while having untradable assets like Seguin and Benn.