I don't care about that, but her loyalty is questioned at this point a bit. 

Our current residents who are AWESOME (rent always on time, take great care of property) now have a situation where the downstairs roommate is moving out but the upstairs group wants to stay (lease is up July 1). 

Not care, introduce legislation to bridge mortgage insurance requirements with lack of providers, get in the insurance market themselves?

Be very careful with arbitrage - run some searches in these forums and you will see the risks associated with arbitrage

Be careful about discrimination if you go the Up To route. 

Sam and I was in a Mastermind together a while ago... although I don't know what he does in his group I can vouch that he is a legit guy and cares a lot about his people.

@Liad AmirFor a landlord in a condo the outside of the property is taken care of like paint, roofs, and landscaping.

More general advice, sorry for not getting too specific, but careful with how you frame your direct mail outreach. 

I've only heard this recently in a book I read, and by a closing agent from a title company.

Read "The House Hacking Strategy" to understand the investment concept.