Thinking most countries in Caribbean including St Maarten will allow citizens to return first as you have indicated.
I believe they will require all who re enter to self quarantine for 14 days.
The next group to enter may also have that requirement. It only makes sense after what the country has went through to get the virus under control.
Would anyone now in US return to St Maarten when airport reopens under the requirement they self quarantine for 14 days?
Guess those who stay for extended periods might consider but do not see the tourists returning anytime soon if they have that requirement.