Sounds like the island isn’t for you.

Lots of very satisfied pilots out there w/ families & I’d say it’s roughly a 50/50 split between homeschooling & private schools. (Never knew anyone to use the public school system.) It’s true private schools aren’t cheap, but there are multiple options & most are able to find one that works well for their kids- though it’s not uncommon for families to move stateside for the high school years.

Typhoons happen. Like earthquakes in CA, tornadoes in the Midwest, hurricanes in FL. Most places have storm shutters & WX tracking is good enough that you get a few days to prepare. There are worse things than playing Monopoly w/ your kids by candlelight once every few years.

Healthcare can be tricky. If you’re generally healthy & just need a decent primary care guy you won’t notice a difference, but if you have any medical conditions that require special treatment, educate yourself about the availability of providers. It can be hit & miss. I have known people to just fly off island every time they needed to see their specialist but that obviously depends on how frequently you need care & not everyone’s comfortable w/ that kind of arrangement.