If I were to take a poll of all of the investors who came before you and who  implemented similar entity formation structures I suspect at least 90% fail to utilize the correct insurance depending on the status of their project (vacant, builders risk, property etc.), fail to execute contracts with vendors, use uninsured and unlicensed vendors, fail to be added as additional insured (likely don't even know the difference between being a certificate holder and being added as additional insured).   

I do have an empty lot next to my current SFH , doing nothing (but costing me money to mow :)) my thought was to build a detached guest cottage to serve as an overflow for guests or it could also serve as a seasonal / monthly rental.

As the saying goes, "in a gold rush, be the guy selling picks and shovels".

With 60 guests a year you are out $240 additional.

I would make sure you really lean into a theme if you're going to do it, because that is what is going to attract guests.

That was the largest part of my financing but in addition I did end up having to ask my older brother to co-sign for me because the underwriters just could not trust the 1099 contractor status given the volatile industry I was in during 2020.

We had a guest that report they were bitten by a bed bug, which they killed and didn't have its remains to confirm if it was or was not a bed bug. 

Daniel Wiafe will be our special keynote guest speaker on Sunday, August 30.

Next year with my pension only I am in the 22% tax bracket but also will have more passive deductions with 2 properties, REP status and cost segregation on both.  

Occasionally, like maybe twice a season a guest would go out and read in the lounge chairs on the deck.