1. More insulation may make sense, but flex ducts are difficult to reinsulate. I would first ensure that your ducts are not leaking at the connections. Leaking air could be cooling the outside of the ducts and creating the cold surface for condensation.
2. Your condensation issues could also be related to the fact that you have excessive crawlspace ventilation -- too much warm, moist air entering the crawlspace. Try to close a few dampers and see what happens. The box fan idea also works when you it is less humid outside than in the crawlspace. The same for the crawlspace vents. Ideally, in our climate, they would automatically open and close depending on the ambient humidity...
3. You may also have excessive moisture from runoff and "sheet-flow" under your house. Depending on how your house sits on grade, a french drain or sump pit may dramatically improve the humidity level under the house. Our clay soils tend to direct water horizontally rather than vertically, especially when the soil is already water-logged.
I installed a french drain at my house on the uphill side and it has dramatically dried out the crawlspace and backyard.
Feel free to write me at anytime, I'm a commercial construction consultant and live on Wedgewood (not looking for business, just happy to advise).
shep.reynolds@gmail.com