I’d just check out comps in the area or talk to a local agent to get a ballpark idea of value.

If they want to bring on a new roommate, you screen them like anyone else and if they qualify, great- you can talk about amending the lease at that point, but that is only a courtesty. 

Thank you. just talk to any mortgage company and tell them you want to come work for them they will tell you what you need. 

Seems like the few people I talked to that are selling land in Florida are trying to sell it above retail without understanding that most of their potential buyers are going to be builders. do Not buy land in FLA without doing full due diligence  on all aspects . there are environmental gotchas that you need to fully suss out prior to waiving due diligence

Happy to talk further on the area (we are large enough to offer options to focus on student rentals/UW Madison campus, and anything from Class C to A locations or suburban/surrounding communities) but to help you consider broad initial search, you could start by deciding how important cash flow is. 

@Jonathan Bremner Happy to talk about investing over here in WNC sometime if you like, to make intros that might be helpful, and to host you at one of our monthly BP meetups in Asheville.

I agree with Joe, talk to a title rep.

They cannot arbitrarily make wild gambles because they feel like it - they have to operate within established risk parameters that are approved by several regulatory bodies and internal controls.

We will buy a single family house like I talked about and then analyze other deals.

Ah, Ok, you have an idea of what we're talking about then.