Not familiar with either Dayton or Philly, though we will become familiar with Philly in the Fall and on the way home no less, but if you have over an hour and knowing your bags should be shipped through to SXM, I’d take the chance.

But at the same time I would definitely take a days change of clothes and swimwear in my carry-on since there’s always a good chance, should the flights run a little late, people will often be okay but luggage? Not so much......