Of course there’s risk. That’s why the return would be minimum. I just think he’d fit well in MTL. Especially if they trade Tatar at the deadline. He can easily crack 50 points again. He’s only 28. He’s not old

I think our only real disagreement is that you stated he would be one of MTL's better wingers, and I look at his age and career trajectory and see him as more of a 3rd liner with some upside going forward.

Wingers who are better: Drouin, Domi (if he plays wing), Tatar (who will be traded), Gallagher. So yeah he’s definitely up there.

Tampa was the best offensive team in the league, and Gourde's production with them would have placed him 8th on MTL, and I wouldn't call a player with bottom 6 production one of a teams better wingers. If he bounces back sure he could push for that label, but right now he is closer to Lehkonen than top 6, and given he broke into the NHL at 26 and has declined both seasons since I don't see him as more than what he is right now, which is a 3rd liner even on MTL who need offense. Also, Armia (who is younger and therefore atleast as likely to repeat his production as Gourde is to regain his form) was better this year also, so that's 5 wingers (Domi or Suzuki plays wing) on MTL next season, again making Gourde a 3rd line winger.
TL;dr, Gourde is unlikely to be top 6, aka one of the better wingers, on MTL next season unless they are a bottom feeder selling off everything they can, in which case they should be using cap space as a way to aquire young assets. This doesn't mean I think he is bad, it just means that I find the statement that he would be one of MTL's better wingers false.
Gourde's less than a year younger than Tatar, so if Tatar's ask is resonable it's a better idea to use the cap space on him.

I’m not denying Gourde struggled this year. But based on the last 3 years his numbers are wayyyy better than Lehkonen or Armia. He’s 28. He’s not 38. I don’t think he’s regressing. I think he had an off year. Habs would be better to trade Tatar and get some future assets while gourde in an expanded role in MTL could help replace his production. 50-60 points is a very realistic point total for gourde. To start the season.

Tatar-Danault-Gallagher
Domi-Suzuki-Gourde
Drouin-JK-Armia

Gives this team a really balanced top 9 to start the year. Though I do believe Tatar will be traded at the deadline. He’s absolutely capable of putting up 50-60 points on that line. I’m not a Tampa fan and don’t care for them. I just think MTL is a good fit for both teams

Based on most stats looking at NHL forwards production in relation to age Gourde is on the back half of his career. He's likely 40-45 points going forward and not 50-60 points. He had one really good year when he managed to make the NHL at an older age than most, and he's dropped off both years since. If he had less term, or there was less uncertainty about the cap, I'd be happy to get him for scraps but 5 years at more than 5M for a guy who has been on the downswing just isn't a good use of cap space. Personally I'd still likely take the risk (I'd be less than ecstatic about it and if I'm the only team he's willing to waive his full NTC for I'd push for retention to about 4.5M), but I won't pretend a 28 year old who's production would make him bottom 6 and has seen a decline the last 2 years should be referred to as one of the better wingers on the team if the trade happened.
I'd gamble that his short term usefulness made would allow me to move him for similar value in a season or two, since I think waiving his NTC would void it moving forward (if not then I wouldn't trade for him) and the cap should hopefully recover with Seattle and the new US TV deal in a few years.