I sort of agree with Shack's take. The Leafs are definitely trying to win to increase revenue not only from playoffs, but via price increases for other revenue streams.That doesn't change anything. We know they can make money now without a winner. A winner increases profits big time.
Being incompetent is totally different than not being motivated. Your original comment of the financial safety net infers they are not motivated which I say is very wrong.
If anything, the Leafs may be guilty of never fully committing to a rebuild when they should have. They spend money to be better sooner. Even in the last 5 years under the Burke regime they made moves to speed up the process to get to the playoffs (unsuccessfully).
And perhaps those teams pre-strike did not focus enough on player development and made moves more to try win at that time. Those were revenue oriented moves -- maybe too short term.
Incompetence and lack of a well defined plan to building are the issues.
Luck / getting hot in short series is also a factor in making the Cup Finals. The Leafs have had 10 teams with over 90 points the last 30 years. That In itself is poor - but it is reasonable to expect one of those teams to once have made the Finals.