I do have some logistics to work out with my renter as they just signed up for another year.

See if you can get a heck of a deal for the ugly house, if it don't workout in the end, see if the owner will let you paint it for them.

This would work out well for me since I don't have cash for a down payment, and the seller is a friend of the family so I could probably get away without making a down payment.  

Well more than anything, I would encourage you to work out the math.

Landlord will likely want a representative to be allowed to be present during communications, but that's up to your lawyer to work out.

Things will work out one way or another. 

A ductless heat pump might work out better and they are fairly easy to install yourself.

I think it will work out fine...

In any case, make sure you draw up a water-tight partnership agreement that details exactly what the contributions/ responsibilities and rights/benefits of each partner are (i.e. don't assume that you are on the same page and that this or that is understood) and that provides for exit strategies from the partnership if it doesn't work out or if one partner just wants out.

On the other hand the properties that I worked for had amenities I couldn't offer like pools, workout rooms, and for those that like the long hallways, more congestion, bigger parking lots, It works, It interesting though they think they are going to use the pool, workout rooms.