I predict this will end in a financial blood bath. 

I need to structure my business for asset protection and anonymity.

Ease of tracking expenses for me and accountants is the other major factor for me on the software.I'm hoping some experienced voices could provide a sanity check, but if we can thread the needle financially this would be a win-win-win at a time when money is only getting more expensive.

Umbrella policies are for added liability coverage when you own multiple assets ( homes, cars, etc).

The objective- Keep your current positive cash-flowing asset in Chicago- Your cash flow may go down if you use a HELOC or refinance the asset, but make sure it's still a positive cash flow. 

If you have enough assets for a roughly 25% down payment plus closing costs the loan will get done.

The 2%  plus charges for listings and photos is difficult financially. 

Is she liable for any damages or personal financial liabilities in which he will be responsible?

Consider converting one property into an STR while retaining the others as LTRs to establish a stable income base, taking into account your willingness to manage STR responsibilities, local regulations, and financial projections for each property scenario.

Currently, I work as a Flight Test Engineer and have come to the realization that I need to do more to secure financial freedom for myself and future family.