I've never actually seen a HELOC where the bank restricts what you can use the money for. 

I guess what I'm getting at is it seems like our options are either bite the bullet in our next primary residence where we are currently located, understanding the future opportunity to rent for cash flow looks pretty bleak, or look in other states where we would have more buying power and try to find a duplex or sfh that will cash flow off the bat. 

Seller Financing:In competitive markets, some sellers may be open to seller financing, where the seller acts as the lender.

And no, it's literally NEVER happened in Hennepin county where they raised property tax's 100%+ because "they needed money". 

Where is the siding rotting and why is the water being diverted to hit the siding? 

@Daniel Stoychev ultimately, Chicago is such a large market that I tell folks to start where you know.

Where on the east coast are you potentially moving?

And the legal fees and accounting fees could be quite onerous.There is another option where you only need 2 LLCs. 

I have no problem devoting hours to research—hundreds if need be—but I really have no clue where to go.

The challenge for most businesses is getting to the point where they can use corporate credit as their primary way to capitalize their business or investments.