Hi Brad,
Yes, the Canon is a piece of cake - no issues whatsoever feeding paper whether from the top tray or the rear heavy paper feed. BUT: you can't have a roll holder with the Canon, and you can't feed stiff material (think aluminium sheets, posterboard, etc.) through a Canon printer. So that's the trade-off. If you never need this kind of flexibility - i.e. only print on sheets, it's great.. no question about it.
Reverting to Epson, and this will also respond to Alan's question, in moving the design from the 3800 to the SC-P800, Epson was looking for a way to be able to give users the flexibility of the roll holder and the posterboard capability in a compact 17" desktop that doesn't have the bulk, weight and cost of an SC-P5000. So this new design emerged from the objective to provide for all those parameters. As well, they were trying to address complaints they had received about the reliability of feeding some fine art media into the 3800/3880. I can't say I'm thrilled with it either and sometimes wonder whether there wasn't another way, but just explaining how all this happened.
Now, the problem you are having using the rear feed is something I encountered once. The sheets were curly. So for those papers where the amount of curl is likely to defeat the roll feed entrance strategy, I found it sufficient to manually reverse curl the paper by gently bending the first few inches of the feed end backwards a few times (not allowing it to crease) and it was sufficient to allow the flow through, so that's what I do if I'm testing a curly kind of paper. This is much less onerous than the tedious procedure you describe. Have you tried that? If you have and it still didn't do the trick, well then you are into a process; but if you haven't give it whirl and see what happens.