Listening to what they have said, watching the moves/lack of moves they have made this year, watching how they are handling Marner and Nylander seeming to still be in the teaching mode and putting their development over immediate success.
Most recently our coach is on the record as having said he wants to win now and force management to make adds due to our good play. If we're to trade JVR it would almost certainly have to be move that does not significantly hurt us now, like say in a package for a D upgrade, but such a move also seems unlikely. Bennet is objectively just making us worse.
As for "Unlikely to win a play off round" that is of course subjective as hell.
This season we are 1-1 with Tampa and 2-1 over Boston. Assuming Tampa wins both their games in hand on us that puts them 8 points ahead of us and this is after an incredibly hot start. That is not a world of difference. In view of our lack of knowledge about who will improve what, who will get injured and who will be hot it's pretty hard to say right now they have a significant advantage beyond playoff experience. Our goalie is playing at a pretty high level right now also.
I know it is difficult for people to come to terms with but the Leafs are now a top team, #6 if I recall correctly. Considering 8th seeds take out #1's all the time it is ridiculous to think we have no chance.
Of course we are not favorites but the favorite only wins something like 20% of the time. No sane GM is going to give up on winning it all before we try, nothing worth having ever comes easy and even if we got knocked out of the 2nd round it would be quite a growth experience for our team.
People need to stop acting like we are a wild card team that is just lucky to be in the playoffs, we are a good team that could very well make some noise come playoff time. We are a better team than the one that gave President's trophy Washington some headaches, so why should we suddenly be afraid of Boston and Tampa?
No logic at all.