See if there is anyway you can help with that aspect of his business.

@Steve Bruza - your post brings into discussion multiple aspects - asset protection, property management, financing, mortgages, transfers, DOS, accounting, taxation, corporate maintenance, veil, estate planning, insurance - all with their individual complexities and interconnected dependencies and intricacies.

Secondly there are 3 major aspects to whether someone is a good tenant. 1.

I also love being part of changing things for the better and rehabs are perfect in that aspect.

There are many other aspects to consider for an airbnb rental vs a "normal" rental.

Lately in MLS listings I've seen things in the agent only remarks such as "Use caution when showing, squatters are in the house".

You can hire a full-service property managerYou can hire a service that assists in the management of the bookings & communications with travelersYou can handle all aspects of your vacation rental property themselves ("by owner".)A full-service property management company (#1 option) is just that: they handle every detail and aspect of offering a property for rent on the vacation rental market, from advertising the property on their own Property Management Company website, to handling inquiries and reservations, key-handling, cleaning and maintenance.

Errol Vincent (real estate agent) helped with advice and suggestions when times got time.Vincent Scherba (property manager) provided tremendous help with putting together a lease and with a lot of the technical aspects I never considered.

Just let them know you want to know about the tax implications as well as the financial planning aspect.

There is for aspects of it, but not everything.