There are quite a few BOS E190 trips to the Caribbean that go BOS - FLL - SJU (or an equivalent way) and bounce around SJU for 3 days then fly back to BOS on day 4. It seems that Boston has more SJU flying than New York. MCO has some, but there just aren't many trips in Orlando due to the small size of the base.
If you're on the 190, you're going to fly more legs per day, no question. Many of the trips are in the NE, and you'll be very familiar with DCA, BUF and BWI. But there are no transcontinental red eyes.
That fact alone makes it worth it for me.