Turn Small Hotel into Monthly Rentals - good idea? Bad idea?

[Anna Christie]

I am looking into a 16 unit hotel that has lots of deferred maintenance and has been renting rooms by the month. Needs roof, paint, flooring, pool is unusable. Location is great, right off freeway and has its own billboard. Besides fix up costs what hidden costs or issues should I be aware of for a old hotel? Are insurance, licensing, or city fees a problem? I have only rented out a single condo before. My intention is to fix this place up unit by unit and ideally rent to traveling professionals.

Any input/guidance is appreciated.