The easiest way to do that is to be honest with yourself about your goals, risk tolerance, personal bandwidth and capital. 

House hacking will also give you some personal "property management" experience.

Overall, he seems to want to do a basic cost seg for me on the FF&E and Capital Improvements and leave the original basis of the property on the conventional depreciation schedule.I would love some feedback, personal experience, thoughts on this matter.

I'm personally a broker and investor doing a lot of work in Davidson county and seeing some good results.

Matt Ollis is the person to speak with.

As a bonus, you can use it for your personal record keeping as well.

My property manager is insisting he only needs one person to sign it given he only needs one SSN on the W9 for tax reporting purposes.

Where to start with guidance and then drilling down what my personal potential is?

Send him a letter, emphasize that you are personally yourself the end-buyer, include proof of funds, include something attesting to you being financeable (unless your proof of funds is for the full cash purchase price).If he owns 20 local businesses, good chance he's in at least one chamber of commerce, and if he's not, he 100% knows people that are, who will spill the beans and offer to do an intro if you mention you're interested in buying a gas station over a beer or a meal (there's probably like 3 people in that city that fit this description, why not get introduced to all 3?)

If I personally understand the skin in the game first hand, I would think this will help me become a better manager of my team on it in the future right?