1) Improving team depth: I don't see this as a huge issue. I'd probably rephrase it as "diversify team depth". I think the Leafs' problems with their depth is a lack of role & identity (specifically the third line probably). We have a ton of talent, and more depth than most teams, but too many of the depth players play the same style, and don't compliment each other well enough to create effective lines, pairings, units, & special teams. Reshuffling to find the right balance of players (I'm thinking most players who are solid defensively) is the bigger issue at hand for Dubas to navigate imo.
2) Goalie situation: This will be a tough one for sure. I'm of the opinion that you should never overpay goaltenders, or give term to players on the wrong side of 30...which both apply to Andersen. A good goaltender isn't easy to come by, but once good goaltenders can quickly turn bad (ie. Price, Bobrovsky...heck, even Andersen this year, although I suspect he'll bounce back), and dishing out huge $ and term to them can screw you over. With a potentially flat cap of $81.5M, and Toronto's current core contracts, they can't afford to overpay Andersen. The question is what the Leafs have in Campbell (some goalies are late bloomers, and he might be one who is capable of becoming a starter), and in Woll & Scott. It will be interesting to see how that situation progresses. Ideally, Andersen takes shorter term & less money until Woll or Scott is ready, but I don't see that happening realistically.
3) Defensemen acquisition: I don't necessarily agree we need a 'top flight' defenseman. We just need a solid d-core that is well balanced. We have two really good defensemen already in Muzzin & Rielly - they just need to be in the right roles with the right partners to succeed. The big concern on defense in my opinion is revamping the right-side with solid, relatively cheap, dependable shutdown defenders. We don't need necessarily need a Pietrangelo to win a Cup, as nice as it would be to fit him in. I think that team defense is a bigger issue than our actual group of defensemen, if that makes sense.
4) Rielly's contract: This isn't a huge concern for me. I love Rielly, but I don't think his contract is as big of a steal as most people think. He's a good offensive defenseman, but his 'breakout' season last year was more a product of good luck than an increase in ability. Realistically, I don't think he can ask for too much more money, and if he does, hopefully Sandin (who projects to be a similar mould of defenseman) can step in to fill his shoes for the right price.
5) Prospect pool: I don't see this as a huge concern if I'm being honest. First of all, I see Dubas & his scouting staff as some of the best in the NHL - they're always on the lookout for market inefficiencies, and seem to utilize this to pick up a better haul of prospects than they should every draft. Secondly, I think development is just as key to prospect success as initial drafting potential, and I also think Toronto's three tier system with the Growlers & Marlies is one of the best in the NHL right now, and we're constantly pumping up quality players through the ranks. Thirdly, Dubas is also great at keeping a keen eye out for acquiring prospects through means other than the draft - see a guy like Hoefenmyer this year, or diamonds in the rough like Marchment & Holl in years past, as well as U24 European FAs coming in to add depth, or develop on the Marlies. Byron Bader's NHLe model predicts Toronto has the 8th best prospect pool right now, and is tied with Los Angeles for the most (8) prospects with a 50%+ chance of becoming NHLers.
6) Seattle expansion: This will be tough, but I trust Dubas knows what he's doing. Every team will be subject to this raiding, so it isn't a problem localized to Toronto, and so long as they don't pull off something stupid like what Florida did in 2017 with Vegas, we shouldn't be overly hurt by this relative to the rest of the league. For sure, we'll probably lose a good depth piece, but so will everybody else.