I have a roller-furling main (and wish it were electric) on a 43 footer and sail alone. I haven't had any jamming issues with the main and have furled it on almost every tack. The forces are lower when the boom is on the port side since the mechanism furls in counter-clockwise and thus the bend angle is lower and you get little friction from the mast
. I do have to control tension on the outhaul
with a hand (or foot) while furling
but that isn't too tough.
Going downwind with the boom on the wrong side is the only time I didn't actually furl since I felt the forces on the furling line were just too much - but all it took was sheeting in the main and letting the boat be driven by genoa
while furling in and then letting the main back out.