There are pros and cons to this arrangement. 

My local REIA has an oil heat arrangement where the landlords who sign up get some favorable terms; you might want to look into that in your area so the tenant doesn't feel like they have to shop around to save a buck.

I'm still doing RE investing (as the business's "real estate guy"), but it sure doesn't resemble the picture I had when I got in.. 

For the secondary bedrooms, expect at least one to be a youth bedroom with multiple bed arrangements.

(You also would split the rent income reporting in the same way.)If you intend to continue investing together, you may want to consider arranging an LLC so that you have more flexibility. 

I can understand -- it may be a temporary arrangement until he finds another place, or she may not want to be tied into living together by lease if things fall through. 

Assessing an issue, calling and arranging a meeting with a handyman / contractor, meeting up at the property, etc.

What are my challenges with this arrangement.

My neighbors would hate it if I had this arrangement.

Then again, I have never arranged a renovation before or yet seen a bid.