Ride on mower collection system clogs constantly.

I have a side discharge mower too and now never use the collector system, it hates damp or wet grass and is just a pain in the you know what. Mine worked fine on really really dry grass but how often is that lol. one thing that does help though if you want to persist with it is to keep the vents on the top of the deck around the mandrels clear so it can draw in lots of air to push clippings up the Shute and where the air escapes at the side of the bins or bags (whichever yours has). don't let it grow long, cut often and go fairly slowly to allow it to blow through. I hope this helps you but I can see you letting it fly free like myself eventually or go nuts with the pipe.

Another thought... check what blades are on it, mulching blades won't generate enough wind in the deck for this system you'd need what I think are called high lift blades.