Hey Mike, typically flies are run behind the dodger or flasher.
I would run spoons or j-plugs off the d/riggers & use your dipseys for flies. I would set them at #2 and run one off each side. Make sure they are set to run away from the boat & not toward the boat. The usual way the guys set their dipsey rigs is to set them up with 1000' of 30# Malin stainless wire with a good swivel on the end. Attach the dipsey with a snubber on the end, then a 5-6' leader to your dodger or flasher, then 23" to the fly. If you're running mono, then a snubber is not really necessary, just keep your drags loose. Be advised that you will have a dickens of a time trying to get the dipsey to release when you go to change lures. The mono stretches quite a bit vs wire which has no stretch. The hot colors around the Mexico Bay area seem to be green/green, white/white, or white/aqua.
Good luck & I hope your son and you both land a good one. Please take the time and gives us a report on how you did in the "South Shore Reports" section when you get back.