Bart,
You are right in assuming that adding more filters to your pump will drop your flow. IME, you lose less pressure if you put your filtration after your pump, not before. Most pumps are designed to push water, not pull it. Fluidized filters usually require a pretty heavy pump, as it has to push through water and sand simultaneously. I would think that running two canister filters, a fluidized filter, and two heater modules would need two pumps. One pump of a reasonable size would be working pretty hard to move water through all of your equipment. All of the added strain puts more pressure on your impeller than usual, and would certainly shorten the life of your pump.
If you're running freshwater, you may want to consider buying an appropriately sized wet/dry filter. You will cut down on the number of necessary "parts" and have more than adequate filtration as well as a place to put your heaters, carbon, etc. However, the setup you have right now would be killer for a planted tank. What would be cool is if Pentair (Lifeguard) made a cylinder for a Co2 reactor. You could put everything under the tank!
I do know for certain that if you are pushing your water through a filter, you are most definately running a pressure system. A flow pump is designed to move water only, not filters.
As far as your return goes, I'm assuming your water is returned at the top of your aquarium, unless it's drilled to return water on the bottom, the middle (both of these practices are rather risky), or your water return wraps around the top of the tank and exits somewhere below the surface of the water. Either way, you want to measure the highest point your water has to travel before entering the aquarium to determine head pressure. On that note, pressure increases as your water turns corners as well. Take into consideration how many 90 degree elbows your water will be turning before it exits into the aquarium.