Like @Ashish Acharya, said there is no holding period and if you're transferring into a disregarded LLC holding period isn't relevant. 

Looks like you guys have a lot of port silt loam, which is NOT a very expansive soil.

Your financial background is a huge asset, and it’s great that you’re starting locally in Milwaukee while keeping an eye on future expansion.If you’re looking to connect with like-minded investors, the Rental Property Association of Wisconsin is a fantastic resource for networking with rental portfolio owners, accessing legal resources, and finding contractors. https://www.aasew.org/For mentors, funding sources, and flippers, the Milwaukee REIA is another great group to explore. https://www.milwaukeereia.com/I’m a member of both and find unique value in each—maybe we’ll cross paths at a future meeting!

In Charlotte, I'd personally on South End, NoDa, Plaza Midwood, Dilworth, Elizabeth, Uptown, or areas a bit further out like Ballantyne. 

FHA 3.5%.You should talk with a lender like @Jose Valdovinos! 

Likely will reduce to whatever market rent is on 1007 report, if the Section 8 income is higher than market.

Agents don't always know what they're doing or they throw things against the wall and see what sticks.Even if you could purchase that, you'd likely face massive coinsurance penalties in the event of a claim since the property would only be insured to 57% of the actual replacement cost.If you've already shopped the policy across multiple companies and brokers, it's likely that the prices you're seeing are the prices you can get. 

I’m open to share my referrals to any who’d like to know.

It sounds like you are overly confident in your Excel spreadsheets..... 

The latter might not let you do anything and is more likely if they don't like your tenants.I see 3 scenarios:The fence is on your property.