Additionally, you have to be disciplined to spend less than you save and keep in mind that you're paying I/O on the principal balance v/s chunking down principal, albeit minimal in the initial years, which goes against the Dodd-Frank rule for qualified mortgages for homeowners

No but you could create an excel macro to do multiple properties at once - also the numbers that someone provides to me I take with a grain of salt anyways. 

We certainly haven't ruled out investing in Wisconsin, but we have friends and family that live in both CLE and CBUS, so we travel to those markets fairly often.

Asking in the correct forum will get a better response.Read the RULES!

Unless new companies create replacement jobs in the city requiring similar skills and pay comparable wages, your tenants may be forced to take lower-paying service sector jobs.

You should consider creating a good entity either way, but especially if you are going to self manage.

LLC Structure: For the LLC structure, would it be best to create a new LLC for each flip, or should I just create one LLC that handles all of my flips?

Be aware that 5 levels of membership can create divisions within the ownership group because the same investment at any point in time can behave differently for each class of investor, so motivations may not be aligned. 

I haven't left more than 5-15K in ANY on my properties and have created a lot of equity in all of them except Toledo.

The 1031 exchange rule to defer your tax is two part 1) reinvest all your proceeds and 2) purchase a property (or properties / DSTs/TICs) with an equal or greater market value.