@Yi Chu2nd option is cleaner, however you will get away with the 1st one, too.The key is to not use this HELOC for anything but business.

I am a seasoned multi-and-single-family property manager in the Charlotte (and surrounding) area.Vendors: I always ensure to connect with at least three specialists in the same field, for example: carpet cleaners/replacements, roofers, emergency services (water extraction or organic growth remediation) this way when it comes time for their services you can get a bid from each of them.

When I change out air filter I can see if anything needs fixed.

My short-term rental is out of state but I manage it remotely (mostly guest communications and troubleshooting issues) and if I include in that the time I spent getting it ready to rent, I would say I materially participated and even more than anyone else (i.e. cleaner).

And he gets to decide how to convey his history and story as long as he is not making it up out of thin air. 

For one tenant that had a cat (inherited tenant and the only cat I've allowed), I had to soak slab with enzyme cleaner, didn't work well, then soaked in vinegar, replaced subfloor boards upstairs, replace trim all around flooring -- it's a huge undertaking requiring multiple applications.     

Digital Guide Books are also great.Boots on the Ground...keep your local cleaners and contractors happy and communicating. 

Walkable distance to Walled Lake Beach and Michigan Air-line trail.

When you purchase a property, you own the air rights above it.

I would never rent an Air B&B with interior cameras.