Evening, I am in the process of acquiring a short to mid term rental in the somewhat local vacation/ tourist destinations in my region.

If you're able to invest in a market where people usually go for vacation in the winter like FL, AZ, Carolinas potentially, then you can get something soon and immediately be renting it and getting a return on your investment this fall.

I'm unsure of how that would work since I would need the current owner to vacate.

My husband fought property management hard, but was angry at the time we spent self-managing as things always seemed to break down when we're on vacation. 

Thinking about using it for our family’s summer “vacation home” and short term rental when we are not using it.

The answer to me is either high end sales or vacation rentals. 

I have quite a few clients who self manage their vacation rentals from the mainland.Here is info directly off state of Hawaii website pertaining to vacation rentals (bold in mine):  If you’re off-island, you’ll need to designate a local contact who resides on the same island as the transient accommodation.

Since you are using the property and renting, you'd want to look into a second home or vacation rental loan programs.

Some coastal cities that were historically very welcoming to vacation rentals (like Rockaway Beach OR) have recently passed new CAP's or rules on STR permitting or vacation rental licenses.

Perhaps you want a “vacation home” and will also rent that out while you are not using it?