If not would you start out buying as a sole proprietor until your investing reached a certain level, form an LLC and elect to be taxed as an S-Corp, or just go ahead and start another S-Corp?

Have a signed purchase agreement for the property with the terms that you want for the seller fiancing Then go to this site https://www.docmagic.com/.You would then find an escrow company in your area to do title and closing ,like fidelity or first american title. 

There has been significant corporate / institutional purchasing in the region in the past 5 -7 years (Hello, Killam ... though they seem to be focused more on Upper Canada now) and a fair amount of "money from away" purchasing smaller properties in this class (ostensibly as a safe place to park capital at a rate better than what it would fetch in a bonds or money market accounts).  

Those are Midwest American numbers right there.

Once I downloaded and digested all that, I went ahead and had them build me a website and give me three months of an American virtual assistant service plus answering service for $600.

FHFA Targets Low-Income Borrowers Daily Real Estate News | Thursday, August 20, 2015 The Federal Housing Finance Agency has released new goals for housing finance giants Fannie Mae and Freddie Mac that aim to widen access to housing credit.On Wednesday, FHFA reportedly instructed Fannie Mae and Freddie Mac to provide additional support to low-income Americans taking out mortgages and refinancing home loans.

There's a handful of manufacturing companies that have corporate headquarters or plants in the area as well, there's also some decent logistics infrastructure in place which makes for a very solid blue collar community as well.

Selling properties for $.30 on the dollar does not meet their corporate goal so they will avoid it at all costs. 

If you operate as a negligent party, maintain a sham operation, and get sued.. no insurance or corporate cover will help.

I am a Certified Public Accountant (CPA) by training and worked in Corporate America for several years as a Chief Financial Officer.