However, when the lease expires in 5 years, if the tenant were to leave, I don't know how long we'd have to wait to get a new tenant, how much renovating the space for the new tenant might cost etc.

@Michael Garofalo hardie plank will keep them out but you have to have a hole somewhere now for them to be getting in. squirrels and mice squeeze through small holes but a racoon needs some space. 

If the space has below-market rents are they going to stay with rental increases after their initial term is completed?

When we hired the 1st coach we were brand new - didn't really know what to look for and the coaching space is pretty crowded and confusing. 

Hoteloperator had additional space.

@Justin Hoggatt I felt that I didn’t provide enough value because I have no experience, so I’m currently messaging local agents and professionals in three space to see if they’d like to speak.

Hunter Thompson is one of the top thought leaders in that space right now.

If I can rent both levels it works, but only the upper level has a rent-ready apartment.The bottom is 95% open space (think large chapel). 

Do not expect to be able to put HVAC duct work in the house if it has a series of add ons--the attics and crawl spaces will have areas that are blocked.Asbestos and lead based paint will be throughout the house. 

Let's start with my single family requirements:In my ideal single family home, I am looking for a 2 BR 2.5 BA with space for myself to add at least one additional bedroom.