The Toronto Maple Leafs entered this offseason with possibly the toughest to-do list of any NHL team, and while the biggest challenge still awaits in signing RFA star Mitch Marner, GM Kyle Dubas deserves at least a B+ for his efforts.

You can bump Dubas & Co. up to an A depending upon taste, and certainly if you’re grading on a curve in considering that every other NHL team was well aware of Toronto’s predicament. Some teams managed to exploit those issues for their own gains, while some still managed to sucker themselves. Either way, mostly strong work so far.

Thursday presented the latest round of moves surrounding that pivotal Marner push, as the Maple Leafs signed Alex Kerfoot to a sensible extension and … meh, at least only signed Cody Ceci for one year? (Not trying, at least outwardly, to merely flip Ceci again and seek a cheaper alternative puzzles me, but maybe Toronto has internal data that argues that Ceci is better than people realize?)

While Nazem Kadri was a better luxury, getting Kerfoot at just $3.5M per year, with some term, is pretty nifty by my eyes. Maybe those eyes have been re-adjusted by the Montreal Canadiens giving marginal defenseman Ben Chiarot that same $3.5M AAV, but I’d wager that Kerfoot will at least be as valuable as his cap hit, if not deliver as a nice bargain.

It fits in wonderfully well with two very reasonable re-signings from earlier this summer, as the Maple Leafs took Kasperi Kapanen and Andreas Johnsson off the docket, getting cost certainty and also avoiding the threat of other teams trying to poach them. For all the talk of Marner possibly signing an offer sheet, the bigger worry might be that an opposing team would instead make it uncomfortable for Toronto to keep mid-level, useful young players. Instead, Dubas got them re-signed, and likely at below market value, even if you take RFA statuses into account.

Good stuff.

Dubas wasn’t flawless in his efforts to get rid of those Marleau and Zaitsev problems, although I imagine that it wasn’t especially easy to find takers to alleviate those concerns.

The Carolina Hurricanes traded for Marleau and eventually bought the veteran out, essentially paying close to $4M to buy Toronto’s first-round pick. If you want an idea of how smart I thought Carolina was, I postulated that rebuilding teams should use that trade as something of a blueprint: basically, take a bribe of picks and prospects to relieve contenders of their Marleau-lite problems.

[ProHockeyTalk’s 2019 NHL free agency tracker]

That’s a fairly hefty price for Toronto to pay, especially since contending teams could conceivably take care of some of the strain of top-heavy contracts by getting quality (or just stopgap) production from players on entry-level contracts.

Luckily for Dubas, the Maple Leafs didn’t need to burn another first-rounder to get rid of Zaitsev’s lengthy, challenging contract. Instead, he was able to package Zaitsev in a deal for Ceci, who will cost the same $4.5M AAV in 2019-20, with the difference being that Ceci’s deal lasts for one year, while Zaitsev’s albatross hangs around through 2023-24. It’s true that the Maple Leafs also had to part with Connor Brown in that trade, but, overall, that’s a comically Maple Leafs-friendly deal, considering how toxic Zaitsev’s contract is.

(The Senators not getting a higher-level return for taking on Zaitsev is, well, a nice reminder that, as much as that team’s plight stems from owner Eugene Melnyk, Pierre Dorion’s also made some rough judgment calls in recent years.)

Time will tell if that blockbuster Kadri – Kerfoot – Tyson Barrie etc. trade ends up being a win, loss, or draw for Toronto, but as of this moment, it’s a bold and sensible example of two teams addressing weaknesses from areas of strength. Maybe Barrie has some flaws, but he’s a drastic upgrade at right-handed defense, Toronto’s biggest area of weakness. If it truly was time for the Leafs to part with Kadri, then that trade was really shrewd.

Speaking of shrewd, I quite enjoy some of the low-risk, medium-reward moves by Toronto. Jason Spezza‘s $7.5M cap hit made things downright awkward at times in Dallas last season, but at $750K, Spezza could be a sneaky-steal. Nick Shore’s an under-the-radar analytics darling, too, to the point that I was surprised that he had to sign in the KHL last season. (Too under the radar, I guess.)

It’s a little tricky to estimate precisely how much cap space the Maple Leafs have left for Marner, as you can see from this Cap Friendly tweet.

With Nathan Horton‘s looming $5.3M LTIR trip, that would put the Maple Leafs over $9M, with some wiggle room with other roster spots (again, see this thread to get an idea of some of the complications).

Toronto being where they are still leaves them vulnerable to an offer sheet on Marner, with these two compensation ranges (via the NHL) being the most relevant:

More than $8,454,871 to $10,568,589 — two first-round picks, one second-round pick and one third-round pick

More than $10,568,589 — four first-round picks (can be spread over five-year period)

Each offer sheet possibility would be interesting. An offer right under that $10,568,589 mark would at least make things a little uncomfortable. If a team wanted to push things into the stratosphere, they could also go well over $10.57M.

Under most circumstances, you’d expect the Maple Leafs to match a Marner offer sheet, yet that doesn’t mean that another team wouldn’t want to really put Toronto in a tough spot.

Theoretically, at least. It’s also plausible that teams a) don’t want to waste their time if an offer sheet wouldn’t work, b) winced at the reaction Marc Bergevin received, c) fear retribution if their big-ticket guys become eligible for offer sheets, or d) all of the above.

Overall, I wouldn’t be too worried if I were Dubas. They’ve mostly walked that tightrope with skill, and could really settle this offseason if Marner just wants to hash things out.

Nonetheless, it’s interesting to see at least some lane to put Toronto in an uncomfortable spot, as the other dominoes have mostly fallen. Could a team try to push the salary up above that $10.57M mark, which might mean that Toronto would have to trade a nice player such as Zach Hyman ($2.25M) to make the pieces fit? Could a team go very high AAV for three years, so Marner’s deal would overlap with possibly needing to give Frederik Andersen a raise, as the goalie’s team-friendly $5M cap hit dissolves after 2020-21?

The Maple Leafs eased concerns about other players by getting Kapanen and Johnsson locked down, so if there’s any chance Marner just wants to get this over with, I’d be inclined to hammer a deal out.

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Even in the unlikely event that Marner signs for the same cap hit as Sebastian Aho, the trio of Marner + Auston Matthews + John Tavares costs well over $30M ($22.634M for Matthews and Tavares alone).

That statement should neatly summarize the notion that, chances are, the Maple Leafs will struggle with salary cap headaches for the duration of their window of contention, if not longer.

As we’ve seen with teams like the Blackhawks and Penguins, it’s difficult to avoid making mistakes, although Toronto will surely hope to avoid trading Teuvo Teravainen and Artemi Panarin-type gaffes, or … doing whatever it is the Penguins think they’re doing right now.

We won’t get the Maple Leafs’ full grade until we see how they handle the final exam that is the Marner situation, but judging by this summer school salary structure session, they’ve been honor students so far.

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James O’Brien is a writer for Pro Hockey Talk on NBC Sports. Drop him a line at phtblog@nbcsports.com or follow him on Twitter @cyclelikesedins.