He has no safety net so I don't think its wise to take the risk because if he did a deal, lost disability and then since hes brand new to REI lets say it takes a while until he gets his next deal I just want to help advise him best!

In that case, you'll strongly want to consider what putting personal-use property inside of an otherwise business-use LLC would do to the liability shield, as well as insurance and tax reporting.There are several considerations that can go into the analysis of whether you need an LLC or whether a large insurance policy will suffice.

Common utilities paid by the landlord will be similar if not the same; standard services (extermination, changing filters, snow removal, fire safety inspections etc.) will cost the same.

For the most part its just health and safety items, which are items we should have remedied anyways.As someone else mentioned, biggest thing to avoid is having the house tagged as vacant which the city will do if it sits empty for too long (handful of months, grass not cut, etc).

VRBO has implemented a policy where they charge a commission on bookings made outside their platform if they can identify them as direct bookings.

I understand that the county is in process of revising policy, but a couple of questions.

This is something you do on your own units policy.  

- Insurance policies (some may not cover rent by room)- Friction among tenants regarding common spaces

I was just surprised that when I asked to change the policy to rental, the first thing he asked was if there was a damage after the hurricane I think a few different things are in play here. 

I do plan to buy a property with 30% to 50% off and have it "acts" as a margin of safety.