Even half retained, I don’t see Dadonov or Drouin getting positive value returns. Use those retention spots on Monahan/Edmundson/double retaining for another team.

You obviously don't follow a lot of hockey, as many as 7 teams have called the Habs this season about Edmundson. His value around the league and many ofthe others you have listed is higher than you think.

Retention isn't an option unless the return warrants using it. It's a waste of a spot and a 7th round pick isn't worth spending the amount of actual cash to acquire.
It's better to use the slot if possible of course, but you're just throwing money away at that point. A good GM isn't wasting their owner's money like that.
Dadonov and Drouin will in all likelihood simply walk to free agency and that's okay. We aren't losing value because it just isn't there.

I would be happy to be wrong, but was feeling pessimistic this morning

Its true, I think the biggest value they can provide right now is walking away in the summer and leaving us all that cap room.

Dadonov has slight value since he still plays ok defensively so he isn't a one dimensional player but Drouin I can see them walking away from in the summer as the only option for sure. There are also reporters questioning a Gallagher buyout since it will cost less than 1 mil for the next 2 years and then 2 mil after that

Edmundson is worth far more.
2 year term low cost at 3.5M Top4 D, Big, leadership, experience, dirty. Like it or not, his value is HUGE because he's such a luxury item. Would every team 'overpay' for him, the answer is no!
But not everyone will spend 100k on a Gretzky rookie card either. There are multiple teams willing to give up serious assets for Edmundson as has been reported by Rishaug, Lebrun, etc.

It's almost delusion to dismiss his value and quote metrics as the sole reason. Nuance needs to be considered here. He's an asset that is scarce so the value increases just like a Gretzky rookie card.

The most impressive thing about Hughes work last year was how he was able to stagger his trade deals. Toffoli was weeks early. Chiarot was done 5 days early then he continued throughout the TDL day. I dont think he can focus much on assets like Dadonov and Drouin NOT that I think they have much value to begin. Edmundsson and Mohanan are by far the two biggest pieces and it will be tough to trade BOTH at market value if not staggered. You have to play so many cards at the same time. Being an agent really proved to be an asset for Hughes last season.

Montreal fans again Sean Monahan will never play in Minnesota wiry Guerin as gm. For some reason you guys don't listen

The Caps already have too many wingers as it is, and with guys playing well like Aube-Kubel and Protas on the outside looking in when everyone is healthy (Which is likely to be soon with Oshie, Backstrom, and Wilson all in regular practice jerseys), there is going to be no room for Dadanov in the starting lineup as he won't push out Johansson or Milano the way they are playing right now.

Also seems like too much for Drouin, I have a hard time seeing any team paying assets for him. Additionally, while I think the Isles would be fine with getting Pulju, I get the feeling that Lou is unwilling to make a move like that (or a move at all).

Would you say there is... wildnochance?

Just curious, why would you say that? is there a history between the two of them? Maybe they hate each other, I honestly haven't followed Monahan's career closely as he only recently joined the Habs and he's played alright but is really just passing through town here ...

Because it's been reported over and over for years since Guerin took over wild by our beat writer including this summer. Literally Guerin wouldn't take Sean Monahan this past summer when Calgary was offering a 1st. There's either beef or bad blood, or something about Monahan we all don't know. So it's not happening