When we fly EIS to STT on Island Birds (small equipment like Cape Air) we deplane and take our luggage to the International customs area. We were required to handle our own luggage - not certain what Cape does. Once you and your luggage are cleared you are released into the outside main airline check in area.

Like Jason I have significant status with Delta. We have used porters in the past with a larger group of travelers but when it is just my husband and I the Delta line works well. If you do expect to use Global Entry make sure you have the actual card. No go without it.