Oh my, what an opening....... First, I'm 80, almost 81, so I'm your elder so pay attention.
(I get to say that to practically everyone these days).
First, about the roller furling main, it should not be hard. I would have a sailmaker check the cut of your main. I had a main on my H27 that had to be sent back to the main Doyle plant and be recut. It worked fine after that.
Second, you need to get a WinchRite. It is a power adapter for your winches so that when you want to unfurl your main, you put the WinchRite on the outhaul winch and pull the trigger and just stand there. I'm serious, it is the easiest thing to do. I have an aneurism on my aorta and should not strain myself. This takes all the strain out of the task. Furling the main (and the jib) is also a piece of cake.
I think a good furling main is us old guys' favorite friend. Have someone check the cut of your main. And let me know what happens.... Good luck, youngster.