I envision this relationship as a two-way street—I'm eager to offer as much value as possible, like identifying potential properties for investment or helping with digital tasks (like websites and social media).I've recently set up my LLC here in South Carolina, but I'm somewhat unsure about the next steps, like where to find private money, locate properties, or structure owner financing for multifamily units.

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? 

I have a good relationship with a roofer who will write me letters saying the roof is good if it is and I replace roofs that are not in good shape. 

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.

Though a cost seg study doesn't increase your chance of audit, if you happen to go to audit it would be very tough to defend as a lay person. 

I plan to hand write the letter to keep it personable and local.

If rent is not paid we follow up personally.

On a separate note, if my personal home and all my business is in the state of Michigan at this point, would there be any benefit to designing the business as a series outline or simply a parent/child LLC set up where the parent LLC would be created in a more tax advantaged state such as TX, WY, NV etc?