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Surprisingly enough, this isn't the first time Kentucky State scheduled a game in the Caribbean-- they were supposed to play Franklin Pierce in Puerto Rico last year. Kinda surprised it wasn't brought up on the board then, but that game fell through for a variety of logistical reasons and ended up being played on Franklin Pierce's campus.
It's a unique strategy, I'll give them that. From what I can find, Kentucky State had established a partnership with Caribbean Athletic Education Cooperative and entered into an agreement to offer in-state tuition to PR residents prior to last year's game. It's an outside-the-box way to try to establish a pipeline and boost enrollment in a time where a lot of smaller colleges are struggling to recruit students, and I think it's an interesting approach.
On the other hand though, it seems a little... Ill-conceived. We've already seen the Bahamas Bowl phased out this past year because of low attendance and complications with international travel, and that was with FBS schools with 5 digit enrollments. At the D2 level, this seems like even more of a headache to pull off to gather a crowd maybe a fraction of the size. Add in the complications they faced last year with Puerto Rico, and I'm just skeptical this will work out at all. Kudos to them for trying to make this work though, I wouldn't mind being proven wrong.