Justify the first purchase by taking the occasional trip down to stay in your rental. 

I have bought dirt that they had tied up and walked away from and they did not get any fee they just lost their 100 to 250k deposit.You can make the argument that commercial companies  may assign a contract occasionally are the same as all these mom and pop wholesalers you see around the country and the states that are cracking down on their methods of selling real estate without a license.

I occasionally hire him for electrical projects, but not in exchange for rent, it is separate. 

Even though your smart lock app will monitor battery usage so you should have the ability to get the batteries changed before they go out, occasionally you may encounter a problem and will want that key for backup.

I've been at it for about a dozen years, mostly on Oahu but picking up the occasional neighbor island property.

They may also be able to find assumable loans occasionally.

The restriction on the main house is a bummer, but being able to rent out 2-rooms, an ADU, and occasionally the main house is a nice thing.

Did you treat it as an investment and occasionally used it? 

Occasionally we get travel nurses, but we're interested in medium-term renters in general.

Stay in your place occasionally.