Maybe have a talk with him before you make any plans? I hope he's someone who loves you as a friend and isnt going to have problems controlling his emotions for you, otherwise, it could get sticky? That way you have some ground rules set from the beginning.

About the furniture, I dont know much. I think the more time you take to sell, the more money you could make? Not always, but if a buyer can tell you're in a hurry, they may use that to thier advantage. Maybe its worth it to you to take a little loss so the timing all works out.

Not to bum you out but I dont know many landlords who are anxious to break leases. I hope you have a compassionate one.
Thanks for updating. Keep us posted!