Tons of outdoorsy stuff too (Metro Parks, Alum Creeks, Hocking Hills nearby)!

Think of all the things that could go wrong and see if the lease addresses them: unauthorized pets or tenants, early termination, security deposit, lease violations, late rent, eviction, lawn maintenance, parking, etc.5.

I would advise to buy all of them because it will make it alot easier for you to put capex money into exteriors, landscaping, fixing parking lot , fencing , lighting , etc because sometimes the hoa might not be collaborative in my experience.

In an congested area offstreet parking might be needed.

Being about an hour from Disney, their reviews seem to paint a picture that there are many folks that stop through for a few nights on their way to theme parks or further south in the state.  

They are built with lots of room for parking, many bedrooms and bathrooms.

I’ve personally house hacked in the Irving park neighborhood in Chicago with a multifamily so not completely relatable experience to what you’re looking to do but hopefully can provide a few insights.If you go with the suburbs in a SFH, you could rent by the room and presumably increase cash flow.

I think the main thing he needs is someone who will counsel him and put the brakes on any foolish ideas.

Driving park is more rentals and would be better for cashflow. 

Great post, thanks for sharing, Kevin--I would also add that the Lower South End area into Madison Park is also a great area to relocated to if you want to be in close proximity to Uptown without being in the hustle & bustle of the city!