This conversation has gotten a bit off topic, but I see the most likely outcome next summer being that TOR brings back two of Barrie, Ceci and Muzzin at a cost of $13M-$15M for the two they sign. I think they move Nylander for futures. That leaves them about $33.5M tied up in their Top 3 forwards, $18M-$20M tied up in their Top 3 D, and $5M for Andersen. That's about $57.5M (give or take) tied up in 7 players, leaving around $26-$27M to fill in the remaining 13-16 roster spots. Not ideal, and they may need to make a series of lesser moves, but certainly not insurmountable. Ultimately, I think they're going to look back in a few years and realize that they either shouldn't have gone after Tavares or should have moved one of Matthews or Marner for a king's ransom in order to build a complete team to win a Cup. I don't think the group of 7 mentioned above can be complimented well enough for them to get it done unless absolutely everything breaks right for them.
I think the biggest issue is the contracts they gave to Matthews and Marner. They are both great players, but it is absolutely unacceptable that they are the 3rd and 5th highest paid forwards in the league AND are only on 5 and 6 year deals. McDavid is the only other RFA making north of $10 mil AAV. Eichel makes $10 mil, but for an 8 year deal. Rantanen came in at $9.25 mil. Aho is just shy of $8.5 mil.
There is just no justification to give those two a combined $22.5 mil. The only even remotely justifiable reason to spend that much is if you got them both for 8 years so you could afford to have a couple years in the middle where you retooled around them. Even then I think that AAV is too high, but it would at least be in the ballpark of justifiable. But with the term they actually got, they have to be all in every year and the AAV should have been drastically lower. The horrible Matthews contract boxed them in to a horrible Marner contract.
I thought Tavares was a pretty good signing and I was all in favor of keeping those big 3 together. But Matthews/Marner should have cost absolutely no more than $19.5 mil combined and that is on the high end IMO. Spending $3 mil more than that is going to prevent them from building the D they need to win a Cup. It was going to be very tough (but doable) at $30.5 mil for the big 3 forwards. I think that extra $3 mil will make it impossible if they don't do it this year.
Going to your outlook, I don't think they can build a long term Cup winner that way. Tying up that much into 3 D pretty much ensures that Andersen is gone after next season and I don't see how they will find a goalie good enough to overcome a still-bad D for cheap enough. Having 6 UFA D men one summer followed by a UFA starting goalie the next is just miserably tough to overcome when you are in cap hell, have a mediocre prospect pool and are already missing a one of your future 1st rounders.
Edit: to swing it back on topic, these type of cap situations remind me just how good our bad signings are. For all the hand wringing about Faulk and Schenn, maneuvering around those deals is nothing compared to the situation other teams are in. Like you said, Toronto is looking at $57.5 mil tied up in 7 guys. That's slightly more than we have tied up in ROR, Tarasenko, Schwartz, Schenn, Steen, Perron, Parayko, Faulk, Binny and Allen for next season. Swap Perron for Bozak and that total is $58.35 for the bulk of our best players as well as every single contract that people don't like on the team. Here's another way to look at it. Sign Petro for $9 mil AAV and clear Allen+Steen while eating $3.25 mil in cap. We would then be paying $55.5 mil for ROR, Tarasenko, Schenn, Schwartz, Petro, Parayko, Faulk, Binny and cap penalties/retention. So $2 mil less than what Toronto is tying up in 7 guys and IMO our top 3 D group would be better than theirs by a larger margin than their top 3 forwards are better than our top 4. Not to mention that we haven't even talked about the fact that Toronto is still eating $1.2 mil a year on Kessel, so our 8 man core + cap casualties would be about $3 mil cheaper than Toronto's 7 man core + casualties. These thought experiments definitely take us off topic, but they underscore the fact that what we complain about with Army's contract issues isn't even close to the crappy cap situations other teams are in.