I assume a simple one page agreement attached to the purchase contract that states the current owner includes all the delinquent accounts with the purchase of the property would be sufficient.

The vast majority of the building is insured by the Condo association but there are usually parts that you need to insured (could be the sheet rocking, cabinets, fixtures, etc.).  

However the vast majority of tourism on this island takes place on the Kona side, which is a minimum hour and a half or so drive depending on where Hilo side you are coming from (if you plan to live in Puna district, like in Keaau or Pahoa area where the cheapest housing prices are, add another hour onto that commute). 

Our contracts typically state "vacant and broom clean".If it's not vacant or if there are new damages, you can do a hold-back of funds sufficient to remedy the issues, but with COVID eviction moratoriums still in place, I would refuse to close. 

Should I be pitching or is just a simple "hey Huckelberry Fin, do you have any interest in investing in real estate", sufficient?

But have sufficient capital reserves in the event of vacancies or tenant improvements!

The vast majority of them could care less.

This sort of deal is probably easier with either one or a few investors, but it is possible there is demand online for pre-entitlement risk projects like this, especially if the subscription price is sufficiently low to get the risk diversified across a number of investors.  

FHA self-sufficiency test is a real thing and can affect your down payment.

If I am using a purchase agreement provided to me by my title company in Michigan and there is no verbiage specifying the contract is assignable, would an addendum to the PA be sufficient?