I will basically forgive jimbo entirely if he actually properly weaponizes his capspace and gets Hossa for a 1st, or even seabrook for a 1st + other picks.
I can see it now tho "We have an extra pick this year in the draft, you know. We got the 6th rounder from the trade last year, we are commited to the rebuild, blah blah"
Just remember that those contracts both count against the cap.
a) Seabrook is going to worse because he's playing, not ltir yet, for another 6 years. Think how many of the youngsters are going to be on their 2nd and 3rd contracts by then ($5-10m each). If Pettersson and Hughes live up the hype that is $8-12m each, plus whoever we draft in the next few years plus Bennings next wave of UFAs. At the time the team is breaking out 2021ish, Seabrook will still be crippling it for years. Now imagine if the 1st you get turns out to be a bust or 3rd/4th liner...ugly.
b) Hossa, will be permanently LTIR'd, he's not coming back, but he still eats up the cap space, and that means rookie bonuses will be harder to fit under the current year's cap and you will be deferring them to the next year's cap which will still have Hossa.
Ideally
1) Ideally you want to be $4+m under for the rookie bonuses every year during this period so you don't get stuck with carry over. 3 years is achievable if they don't waste money on 4th liners and fill up the cap so you can burn the bonuses the year they earned.
2) you can use the space every year if you don't lock it up for long term deals, a series of short deals and 1 year UFA signing may give a better return.
3) having cap space could be useful in the long run if a good UFA comes around at the right time, having it all locked up in long term cap dumps could cripple your offer. I'd rather have 6 2nds than 1 1st unless it is a great 1st (we aren't getting one of those).