Please note the information provided below is a layman's definition designed to provide a basic understanding for the general audience.

Operating legally is definitely not a safeguard as I provided data to the city that was sufficient to demonstrate that it had operated legally at least the last 5 years (but it has operated legally 23 years) to get maximum STR lottery entries.Note this quota occurred after the council initially passed a ban on STRs all together and pulled the regulation when it qualified to go to ballot (council must have expected they would lose the ballot initiative why else pull it without having it go to vote). 

Other factors that you should check are:1. does the citizens policy provide better coverage than the separate policies or the reverse2. how does the claims paying ability of citizens compare to the two separate policies3. is either more likely to renew coverage 

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.