anyone would think this deal could work with the limited information I've provided :) ? 

If you could provide a general overview or a step-by-step guide at a very high level—focusing on vacancy rates, capital reserve expenses, expense ratios, and any other crucial details—it would be greatly appreciated.

This is doable however my time to find, procure, and renovate rentals is very restricted due to my life on active duty.When looking strictly at the numbers a mortgage provides a better CoCR and a better ROE, but stepping back and looking at more plain facts it seems like leaving the house paid off is the best bet, thoughts? 

All of my rental properties will be going into the business on the property management side which will provide the company immediate income.

The main benefit of an LLC over home insurance is that it provides personal liability protection, so if something goes wrong, your personal assets are safer.

But most importantly, I’d like to connect with other like minded individuals As one of the other people mentioned, an umbrella policy is one of the easiest ways to provide yourself with protections from a liability standpoint.

These are more complex legal structures that can provide even more protection than a traditional LLC alone.

She says her renter insurance will provide liability coverage up to 300K.

I am not providing substantial day-to-day services.

I'd be happy to provide any insights I can into the process and what to expect in the Chicago markets.