If we were guaranteed one of Matthews or Chychrun, I'd rather finish dead last. Like with McDavid/Eichel this year. But there is no magic wand and there is no guarantee, not even under the old system. It is hard to try and finish dead last because there are always a few other really bad teams out there too.
Now, add in the new lottery system where even if we do finish last, we still have a very good chance to pick 4th. And it is STILL hard to finish dead last. So if we finish third last, we have a great chance to draft 5th or 6th. To me, hoping to lose for an entire season is not worth drafting 4th or 5th or 6th. If that's what ends up happening, great. Who wouldn't love another 5th overall pick in their system? But during the season, I will hope for our current Leafs to improve, and by extension, win. The new league just isn't set up to tank anymore.