It does feel like there is likely a major market correction coming, but due to limited inventory of vacation-rentable units in Maui I feel like I should be somewhat more protected from the effects of said recession.

All that combined with limited building and no state income tax there is positive rent and appreciation. 

As mentioned, they often come with limited returns and still require management.I’m curious—when you say active investing doesn’t appeal to you, is it because of time constraints or concerns about risk?

So if you are selling a property in a given year, it might be worthwhile to talk with your CPA and see if selling some stock at a loss would be helpful (since otherwise capital losses are limited to $3,000 as Joshua mentioned). 

With your skillset and limited finances, it might be great to be a small partner on a deal with another flipper or be some of the work on the deal so you can see how it feels time wise.

Because of this, I believe the market for selling my houses is likely limited to other investors.

Consider creative approaches like short-term rentals, ADUs, or co-living spaces that maximize income in limited spaces.

Passive investing takes time up front to educate yourself, find operators and deals - but after you invest, you have limited obligations.  

You want to appeal to the most people and many buyers will want to live in the home, so having tenants will limit who it appeals to.

Your current plan seems like a lot of sacrifice for limited gain.