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.

@Gillian Thackray It's actually quite surprising the PM you use is not effective or perhaps not motivated to perform the leasing duties effectively but appear to be fairly competent with the day to day management services.

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

STRs and MTRs are a lot more effort than LTRs and my STR/MTR units are not currently performing well enough to justify the increased effort.  

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? 

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?)

Also, while I've read some horror stories about assessed value increases, our personal portfolio came out relatively unscathed during this recent batch of tax bills.