Hi Nick,
I can't claim to have many answers for you but I can bring up some details that may be important factors to include in your deliberations. I'm a small time investor in Minneapolis (triplex), with a long-term SFH rental in south Kona I hope to early-retire to, and my folks have been living in Naples, FL since the mid-90s where they've funded their early retirement with long-term rentals of condos. You are smart to consider all this as a choice of your own home, with potential to off-set your personal living expenses with rental income.
#1: Warm water and warm weather
It all comes down to personal preference but to me, as an avid snorkeler and SCUBA diver, there is no comparison between Hawai'i and these locations in FL. Some parts of the FL Keys would compare. Have you spent time in all these places and feel like you have a sense of the local culture? Are you going to regret moving very far away from friends and family to HI? Life on an island, especially one as small as Maui or as small population as Hawai'i is very different in subtle ways that you might not notice while on vacation. Many Hawaiians don't bother making friends with newcomers because it is so common they can't hack it and go broke or get too home sick and return to the mainland within a year.
Remember to factor in that with warm weather and warm water also come risks of storms, flooding and hurricanes. FL has taken a real beating in the last few years and looks like it will continue as the climate warms. With some elevation on west Maui and west Hawai'i it more rarely has these issues but do have a history too. Look at insurance rates, and the uncertainty of future insurance costs and factor it in.
#2. Schools
I don't have kids or work in Ed so don't know much about this but can tell you I see a lot of educators in HI complain in the neighborhood FB groups etc. about low wages compared to the cost of living. COL in HI is a huge issue in general. Food, utilities, gasoline and housing are all extremely expensive. There are online calculators to show you the comparative COL. Be prepared that you may need to make major lifestyle changes in order to make HI affordable. Buying is similar cost to southern CA though I feel there are better deals and less competition to be had for places needing remodeling. Try to reach out through professional and neighborhood groups and get a real sense of what pay vs. COL in HI is like.
#3. We MUST house-hack
There are lots of investment properties that meet the 1% rule to be found in FL. But they may not be MFH or a place you want to live with your family but finding cash flowing properties should not be a huge challenge. HI meanwhile is much more expensive to buy and local incomes can't generally support reaching the 1% rule. Vacation rental will get you much closer though but there it gets sticky with local regulations/neighborhood covenants, changing regulations and tying your priorities for a personal residence together with properties that are good performing vacation rentals. The prevalence of "ohana" units in HI opens up lots of flexible options though. I wouldn't want to buy a place if I MUST have the higher cash flow as a vacation rental or it would be unaffordable.
Things I learned are important to know when buying in HI:
1. types of utilities (solar? -- is it leased or owned, just for hot water, is there whole-house battery back-up?; is the water city or catchment?; Is the sewer city or cesspool or septic?; anything on propane?)
2. leasehold vs. fee simple ownership
3. is internet and cell service available and reliable?
4. is the area dependent on a single transportation route in and out (likely to get stranded when there is an accident on the main road)?
5. What lava zone is the property in and can I get HO insurance?
6. What are the local laws and neighborhood covenants on long and short term rentals? Are they considering changing them?
7. Dealing with stuff we don't have in MN - vog, termites and earthquakes
I can also recommend the podcast called Afford Anything. 50% of the episodes are answering listener questions and 50% of those are dedicated to REI. The host often walks through ways to think about options like this and how to wisely separate investment decisions from personal lifestyle decisions.
I hope this is useful to you. Feel free to message me if you want chat!