I don't know which Leafs fans you are referring to but I doubt whether any of us are making assumptions about making the playoffs given the nature of the opponents that they have to play five times in seven days to finish off the season. They include the three best teams in the Eastern conference and what is likely to be a full strength Tampa side which was good enough to make the cup final last season. That won't be easy. 
What relevance does the past have to this though? In case you hadn't noticed, the current ownership and management have not been around for ten seasons. I had misgivings about Bell and Rogers taking ownership of the team but, to date, they have allowed the managers to run the show and agreed to pay big money to deal with the mistakes of previous management. The team has now cleared the deadwood and is way of ahead of where they would be expected to be  at the end of last season. The previous seasons are irrelevant; what matters is how they have played this season.