This has been my thinking. DW needs to add two top 9 wingers, at the very least one being a solid top 6. Between that list, buyouts, and trades from teams wanting to make space he should have ample opportunity to do so.
Dadonov, Smith, and Fast would make sense in ufa. We should put aside pipe dreams like Hall unless DW surprises us by trading Vlasic, then all bets are off (though the odds of him wanting to sign here are slim). Players like Ryan would be perfect to round out our third line, anything bottom 6 needs to come in at bottom of the barrel price. Someone like Namestnikov could be good depth but I'd rather the team devote more resources to higher potential reward. Don't completely discount aging players or reclamation projects like Kovalchuk or Galchenyuk.
The trade market is where things could get interesting. Depending of how much cap we can unload, and if that's the direction DW wants/needs to go, there are quite a few great options out there. Nobody knows exactly who is available, especially this weird year, but winger is the most plentiful position and there are tons of teams looking to shed cap. We've discussed Domi and Strome. Ehlers or even Laine could be had, though it would require a much larger price going back. The Jets need a right top 4 d and a number 2 center, we could offer that but the pain would probably not be worth the gain. Something around Ehlers would probably be more doable/preferable than Laine and would be less likely to involve a player going back. Kessel is an interesting name going around with the Yotes looking to shed salary, but it's unknown if ownership would want to cut bait so early after their big get. Killorn or Johnson, somebody is getting traded from Tampa. Johnsson is probably available in Toronto. Anderson might be moved by Columbus. The there are a ton of completely unknowns, teams will move rfas, teams will dump salary, there will probably be more churn this year.
DW seems to think we need to add to our still good core, so it depends on who he views are essential to that(Hertl, Couture, Burns) and which players would most benefit from what. Dadonov probably offers the most offense and can make plays in the top 6 while someone like Smith is more of a trigger man who can play anywhere in the top 9 and round out a PP. These aren't necessarily game breakers on their own but they fill in the gaps that were so glaringly missing last year. Killorn is another that could play anywhere in the top 9. Ehlers is more elite and could have instant chemistry with Timo, but would probably come at too much cost.
The hope is that DW knows this is a make or break season. I think he sees it the same way he did the last time the Sharks missed the playoffs when he added Martin and Ward, with maybe slightly more urgency. Martin and Ward were big adds, I think people forget how big. Martin was a solid top 4 d, probably a number 3 who could play with our best d at the time. He made our d core function when Burns hadn't yet completely solidified into his Norris form. Ward was a super solid top 9, incredibly sound in all three zones, who scored 20 goals for us that year. If the Sharks add two quality wingers, get solid depth from players like Gregor, Leonard, or other prospects, and our injured/slumping players return to form then we can get back to being a playoff team and this long nightmare can end.