mediocrity treadmill. You want to try and win now AND later. The problem is that the number one thing the Raptors need more than anything is a franchise player. They're not going to sign one, and they most likely won't be able to trade for one. The most realistic way is to try and draft one, which means a high draft pick next year, when there will be a strong draft.
And the reason the Raptors and other teams are where they are is not because they didn't hedge their bets. It's because of lack of good management and/or luck. The best teams are where they are in large part to the fact that they have a top ten player on their team.