Sometimes these insurance contracts come in legal sized paper- possibly a harbinger of what you'll need to do to collect fairly from them, But always expect them to perform completely on the things which are in their financial favor.

What is the optimal way to proceed?!

I don't provide alcohol, but I sure collect a lot of it after guests leave!

Need to optimize my current real estate holdings and looking to add more properties.  

Ideally I want the money collected to be accounted in the month I'm paying the mortgage so I can get a better sense of my monthly cashflow month over month, but that means I will need to record the draw I receive in October in September so things all line up nicely.Anyone have any thoughts on that?   

No penalty to let project die slow death and collect salary, travel and advertising money from it.This is data, everyone should make their own data driven decision based on it.

Also, focus on 2 years of job/income stability.Class D Properties:Cashflow vs Appreciation: Typically, all cashflow with little, maybe even negative, relative rent & value appreciationVacancy Est: 20%+ should be used to cover nonpayment, evictions & damages.Tenant Pool: majority will have FICO scores under 560 (almost 30% probability of default), little to no good tradelines, lots of collections & chargeoffs, recent evictions.

;-)I have owned and rented SFH since I was in College (I bought my first home, and then lived in it while collecting rent to pay the mortgage and make cash from my roomies.).

And unlike HOAs most are not going to flat out ban STRs, but rather try to collect taxes/fees from those that want to run them.

Most of them now have some sister entity established so they can collect premiums and then file bankruptcy and leave when events occur.