IMHO - whether we sign Stamkos or not (I don't think it'll happen, but I didn't think we'd get Babcock either!) .... I see this rebuild shaping up on a set timeline that's maybe not as long as some are assuming.
We currently have nicely stocked cupboards, but not enough prospect depth that we dip into the pool if needed to improve the team without impacting the long term.
I see this year has been set up as a transition year - the prospects will kept down, and the roster will undergo a little bit of chaos with players being shipped out throughout the season.
By next draft, at least some (not all) of our existing core (Bozak, Lupul, Phaneuf, Kadri, JVR, Reimer / Bernier) will be moved out for future assets. Some of the one-year wonders will be shipped as well, with others whom Babcock falls in love with being resigned to short term (1 - 3 years) extensions. We'll likely enter the draft with at least 13 / 14 picks, and likely a few more for 2017.
After the draft, we'll have a top 5 prospect pool, with enough depth to use some of those assets if the right opportunity comes along (read: Saad / Hamilton type RFA a team can't sign). The team will be pretty much completely torn down, and management will know exactly who they want to keep long term (possibly Kadri, Phaneuf, Bernier or JVR depending how they respond this year).
With the team on the upswing and with a more positive environment even through the chaos - we'll be a more attractive FA destination, but I can see management refusing to overpay - there is nothing like winning in Toronto, and if you want to be a part of it, you'll have to leave money on the table.
For next season, I can see Lou using some of the asset wealth to target a good young player or two on the trade market, add some solid vets via reasonable deals in free agency, and the promotion of a number of NHL ready prospects such as Nylander and Brown.
The tear down will be over, and it will be about "building" rather than rebuilding - with the team likely improving year over year starting the 2016/17 season (not saying playoffs - just that the team will be moving in an upward direction).
We're not starting from scratch here - and already have some fantastic pieces in Nylander, Marner, Reilly, Brown, Kapanen, etc. I can see us being in a position to do some damage by the 2017/18 season with the right moves.