I have tried to operationalize it as much as possible with Notion and Trello but things are still falling through the cracks (SOWs taking too long, units not being listed, etc.).

The cash flow was good from day 1.

Obviously property management is not for everyone but for those who treat it as a separate business venture, it could become beneficial in the long run. 

Always good to meet more Maui based investors.

Being pre approved is great but good agents will need to know more so time isn't wasted with properties that don't make sense

Airbnb handles the payment so I don't worry about it and I've found that the typical tenant that is willing to pay 2x the LTR rate is going to keep the property in good condition.

Boat and RV storage is at a premium for many people so you have a good idea to use existing land to generate income without doing too much in the way of improvements.

For the e-cigs....With the other documents, new child will sign the no smoking / vaping addendum, that might be a good way to address anything without saying "hey I saw a pack of e-ciggeretts on the counter". 

I manage a couple of rentals on the side (one long term and one STR).

Good Luck!