If it were me, I would go with the plan that leaves you in good shape no matter if the Habs rebound quickly or not
There was nothing great in the Phaneuf trade for sure, Lindberg had a chance to be middle 6, and the pick that became Rasanen is still unknown. The roster pieces were nothing great, but they were something to ice to protect the kids and face the media when the team was terrible. I agree that it was a very good return at the time because we got out of the contract without retention. Phaneuf is probably a worst case scenario for what Weber could be when he's back, but he'll also be 5 years older than Phaneuf at the time of the trade so I would take something like that if I got a couple of lottery tickets like Lindberg and a pick out of it (in the case that Weber has regressed when he's back). I also never see the point of keeping a guy for the sake of eventually getting nothing back and watching that guy retire, I always like to manage assets
If I had the choice, the Leafs would have traded JVR & Bozak last summer, and we'd be trading Gardiner this year if we're not going to re-sign him. So maybe my outlook is biased on Weber, but I don't get the point of keeping him if eventually he just retires a Hab or gets dealt for nothing if he goes to a cap floor team when his salary reduces. I think there's a side benefit of him being gone too, the team will likely be worse and will likely draft higher