I’ve seen some light scratches on floors and extra hair cleanup, but honestly, it hasn’t been anything major when there are good systems in place.

I personally would go with a property manager simply because they're far more experienced at that sort of stuff than I am.

Just got the unit back right before finalizing the eviction to discover that they had been scamming multiple TV/internet providers for the free 3 month sign on period and then switching to the next as there are about 6 different companies boxes that I have to sort through and return as occasionally they stick the bills for equipment with the landlord in our area.

Cleaners charge me an extra $25 and if excessive hair to clean then charge $50

You will be best served on the outskirts of Nashville as city limits will have more restrictions on this sort of project and also less of the vibe you're trying to achieve. 

Quote from @Becca Brown: This is a sort of litmus test for me, so please be honest (but kind lol): What are your thoughts on AI in property management?

If you have the rec room outfitted with some sort of kitchen you could market as a studio or if a less than full kitchen maybe call it an efficiency which implies a kitchenette.

As far as his office equipment, he should carry a policy (renters) or some sort of business policy to cover their items. 

[2]      Do you think you need mostly office space, or mostly kids training space--like a karate floor sort of situation or something; But it's soccer so wouldn't this most likely be an outdoor field and not a building? 

Hi Linda,Lots of great advice from @Carla Gordon @Brian Schroeder @Jay Thomas Specifically I think it's always smart to check out FF Traveler sear https://www.furnishedfinder.com/housing/New-York/New-York) and Airbnb/VRBO for 30+ days stays to gauge what sort of similar properties are currently out there!