IMO, the Wings moving a goalie before this seasons deadline seems unrealistic unless:
A. They're getting a goalie back in the trade - Either a throw in the Wings can use in the NHL behind whoever remains of Howard or Bernier, or a throw in/prospect that can start in GR if they decide to call up Pickard to use as #2 for the rest of the year.
B. They plan to or have already acquired a goalie in another trade before the deadline - Same premise as above, but they came in a separate deal either in a deal for a skater they're trading as well or specifically to acquire a throw away/depth goalie from another team (of which Yzerman's former team has a wealth of, including one taking up NHL cap space)
C. They (or GR) sign someone to replace Pickard in GR so he can finish the year on the NHL roster, and GR can stay in mix for the AHL playoffs
D. GR has no hope of making the playoffs, so they're fine calling up Pickard for the rest of the year and letting whoever's still there split the rest of the starts in GR
E. Someone has offered a ridiculous overpayment for Howard or Bernier
I don't see a whole lot of contenders wanting Bernier because of his salary and term. Especially Toronto, who will likely have to roll with another round of "waiver goalie roulette" next year to have enough space to re-sign/replace all of the forwards and dmen that are free agents this summer.
I also don't see Yzerman tanking GR's playoff hopes so he can get a late 3rd for Bernier.
With Howard, you're looking at something like Kinkaid's 5th rounder three years out or the Flyers and Oilers Stolarz for Talbot, and that would be with Howard at full retention.
As for some of the skaters that could move, some of the return predictions here seem super pessimistic...
Here are some comparables for bottom of the barrel D that was traded before last years deadline:
NJ traded to 35YO rental D Ben Lovejoy to Dallas for 24YO D Connor Carrick and the Stars 2019 3rd (that ended up at #80OA)
Sabres traded 26YO Nathan Beaulieu (basically a rental as an overpaid RFA unlikely to get qualified) to the Jets for the Jets' 2019 6th (#175OA)
Ducks sent 28YO rental Michael Del Zotto to the Blues for the Blues 2019 6th (#186OA) - Del Zotto had been traded to the Ducks earlier in the year by the Canucks for Luke Schenn and a 2020 7th
Kings sent 27YO rental Oscar Fantenberg to the Flames for a conditional 3rd or 4th in 2020 based on where the Flames end up in the playoffs and Fantenberg playing in atleast 50% of those games. The Kings ended up with the 4th.
Boston sent 32YO rental Adam McQuaid to the Jackets for throw in contract Julius Bergman and Jackets 4th and 7th picks in 2019 (#112 and #205)
Green - Even with his down season, he is a clear cut above all of those guys, so if all he returns is a 3rd or a 4th, I'd be kind of disappointed in Yzerman....
That being said, I think what might hurt return on Green is another longterm injury, or him getting weirdly picky with his 10 team no trade list by listing a bunch of contenders that might actually have interest... Remember two years ago, he reportedly nixed a potential deal to the Leafs, and really only seemed open to going to Tampa or back to Washington. Now two years older, more broken and with a bigger family, I can't imagine he's much more open than he was then. Since players usually aren't big on going to Edmonton, I'd be surprised if Green wanted to go there, despite the familiar face running the show there.
Daley - I'd imagine he's somewhere in the Lovejoy/McQuaid return category, especially if he's healthy at the deadline and even more so if the Wings retain. I think the fit for Daley is a spare vet D for a playoff team and/or an insurance policy for a playoff team that has some young D they may be worried about trusting in the playoffs.
Helm - IMO, he's well above the "conditional 7th" territory, especially if the Wings retain enough to get his cap hit at least below $3M if not more. That said, I don't really see Helm moving until the offseason or next years deadline.
Glendening - Probably at least a 2nd or a 2nd+ depending on how many teams are trying to get him
I have to think Yzerman will try to get the NHL roster down to 12F and 6D from guys that are currently on the roster. That way they don't have to burn a call up on someone from GR to fill the roster, but can give a whole bunch guys looks using the perpetually banged up nature of several of their vets as an excuse to give a handful of different guys looks using emergency recall. I also wouldn't be surprised if Yzerman cleared some room because he knows he'll be bringing in an undrafted college UFA or two to burn their first ELC year ala Hirose and Kuffner.
