The nuances in state regulations require an expert who understands how to expedite the process within the legal framework.

I would keep it in a high interest bank account might as well earn as much gain as you can no matter how small it is.However I think some debt pay down would be great not to the point where you are not liquid enough to Jump at another opportunity or can’t make a major repair when it arise.

It can still qualify if it's a fixer-upper, as long as the rental income from the property can cover the debt service.

.❌ Legal Risks – Chicago has strict landlord-tenant laws.

If the bank will call their note if you commit to the transfer you can also check out this article as one strategy that has been used to work around the issue.This is not legal advice, just my opinion as a real estate investor.

I  Income:  The amount of property you can buy will be dependent on your Debt to Income ratio.  

Now this is with an uncontested legal action..

Hi Anthony, it sounds like you’re in a good position to start building your STR portfolio, especially with no debt, great credit, and rent-free living!

I think hard money lender to take this risk cannot legally charge appropriately which means the law is working against you (the law meant to protect owner occupied owners from unfair loans).I agree with @Jay Hinrichs that your best option likely is to sell on the mls.  

There is no requirement for @John Gillick to replace debt with new debt.