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. 

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?

I think many of us use hyper-consumerism as a means of validating our self-worth.We NEED to upgrade to a new cell phone every year, we NEED to take expensive vacations to show our friends how fun our lives are, we NEED to purchase the more expensive car, we NEED to eat at chic restaurants and document the experience all over our social media.

Revisiting the subject of financing for vacation home/vacation rentals/STR's.  10% down is still an option without having to pay points.  

Here is an article from 2022 - https://www.lakeexpo.com/news/politics/vacation-rentals-in-j...It talks about the judges ruling about certain homes not being STRable.

Initially I had a feeling you didn’t really know what you’re talking about but now it’s crystal clear you have no idea what your saying and you are more than likely just another misleading , Detroit PM nightmare like 99% of the other PM’s in Detroit with all sorts of hidden fees, secret add-on’s who work against the tenant rather then with them so they end up vacating and you guys salvate over another nickel and dime placement fee.The question ‘why’ in your first comment has absolutely NOTHING to do with it I am simply sharing my experiences.