I don't see any trade making sense that CBJ get more for Bob than he's worth, even if he is only here one more season. I'll keep saying this - I'm fine with kicking this can down the road another year. Don't trade him, don't re-sign him. Play out the year and then decide.
The two sides are talking, so for the moment they are taking your suggestion. Having said that, if it becomes clear he's going to test FA you have to decide if you think the team can go deep in the playoffs (legitimate cup run) and if you can sustain that level of play after the goalie leaves.
It does you no good, other than limited financial gain, to just roll with it and let him walk for nothing if you aren't in your "window". I have reservations about how good this team really is. Without two amazing winning streaks the last two seasons our play is otherwise kind of pedestrian. Most of the board basically says we have no chance without Bob. If that is the case and you can't re-sign him (personally I don't think this will be an issue, I think the FO will be desperate), then you better start taking a serious view on assets.
Frankly I think you wait until the deadline even if you can't re-sign him. That will make the cap hit far more manageable for the rest of the league. At that point if you are just hanging on to a WC spot (or worse), just move on if there is a decent offer on the table. You might need to make the same decision with the other franchise level player. We might end up in a mini-rebuild scenario.
The reality is we have our top pairing D and the rest of the D is respectable, even if I'm not a fan of Savard. It's certainly not as good as our fanboys were making it out to be last season. Where were lacking is forward, mainly because we have 3 forwards, making around 16 million, that aren't doing a whole lot right now. Actually make that 20 and include my boy Jenner.
It doesn't make things easy on the FO when your team performance is all over the place and you have a goalie that hides issues.