You can't make too firm of plans on that second window until we know how this window will be opened...i.e. if we get Hughes, can kidnap Stone, & Makar is a norris candidate as a rookie; then how much & what kind of supporting talent we'll need during the 2nd window, as well as what sort of tools we'll have left over to address it will be very different than if Makar struggles to be any better than Barrie & Girard, and we trade the ottawa pick++ for Larkin after the lotto gods screw us, and can do no better than a Silverberg-type in FA...and much of the preparation for a 2nd window can't be done before the 1st window has opened; as NHL teams just don't trade picks that far in advance.
But we can adopt certain strategies that favor the opening of a 2nd window by a) having an initial window in the first place, with which to attract talent & convince MacKinnon to even sign a next-contract with us; b) selling off pieces that we won't be able to afford over the coming years; c) taking advantage of our improving organizational depth to focus our drafting on high-upside long-term projects...of whom a few may even deliver...that we won't have to rush into the league ASAFP; d) moving back for future picks when there's no one you're in love with & using our pick surplus to upgrade picks into that top 40 range where you're much more likely to find contributers...at least in the latter stages of window 1, when we're starting to really get ready for the Retool...and; e) by only dipping into our asset-surplus for real long term solutions...aka unless we're ready to win the cup, mother**** a rental, only touch that surplus to roll it over into even more futures, for a legit 1st liner, #1 blueliner, or top tier goalie...and ideally only for guys who could be a part of both window 1 & window 2.
If Mikko gives us a bargain & signs for something that begins with a 9, that'd help, but we're still going to be spending at least 20M on he & Nathan's next contracts unless things go horribly wrong for us.
And unfortunately, a 2019 draftee...even if they don't make the NHL until their draft+2 season...will no longer be on their ELC in 2023-2024, when MacK's new deal will kick in. So that Ottawa pick -- assuming it doesn't bust -- is actually going to make the cap crunch trickier, rather than easing it, by adding another RFA that will hopefully require a big extension. So the Ottawa pick could be a huge part of windows-1 & -2, but it's unlikely to make the retool easier.