I can see why you'd get good cash flow! 

Most any major metro area is going to have good demand for medium-term rentals.

Definitely a good overall real estate market with solid upside potential. 

Personally, I wouldn't open up a home that isn't in good repair, from a liability standpoint if nothing else.

Quote from @Don Bessette: I have a 30 plus year tenant that can not keep up with maintaining their unit, it is filthy inside and in desperate need of renovation, all systems are in good repair and I respond very quickly when issues are brought to my attention.It is also well below market rent, and they struggle to pay the current rate.Looking for suggestions on how to gently proceed with the notification to move. 

Try it out first test out whether or not you two are a good fit before building a massive portfolio together.Create an operating agreement for your LLC, and create a partnership agreement, defining roles and expectations.

(Good Choice!)

This seems like a great fit for me other than the fact I cannot find a company that has modestly good reviews.

If no one but owner-occupants can STR... then that should mean opportunity for owner-occupants who STR their primary residences in many jurisdictions.- Large remodels or construction projects (Live in Flip) can be self-managed, worked on directly, and the value add, after 2 years, is largely tax free up to certain limits. - Many areas around the country allow for ADU Construction - house-hackers enjoy similar benefits to remodeling projects by being naturally on-site for ADU construction. 

Develop a good BS Meter!