Hard to say. The realistic nature in me, sees the Isles overall organizational standing and thinks it would be best to get in this year's draft lottery while gaining another possible first and/or seconds from selling. Then translate some of that to a further retool in the offseason
But once game time comes around, I'm all about wanting them to win. If Lou does buy, I hope that it is at least with an eye towards further shifting the core. Does not necessarily have to be a player that is signed or extended for next year... but at least have some salary (Bailey, Palmieri etc.) going the other way. This allows for shifting that to someone else this offseason.
EDIT: But to actually answer your question... I think he buys.