Things to try:
1) Be sure you're pointing directly into the wind.2) Be sure the vang and main sheet are released and free to run, otherwise they will make it hard to raise the sail.3) Try some McLube "Sail Kote", it's a teflon spray that helps quite a bit to reduce friction on the sail track.It really shouldn't be TOO hard to raise the main. I've got a 340 which is pretty much the same boat you have and can often just haul it up without a winch at all. If it's super hard to crank up better stop and figure out what's wrong, you don't want to break anything... If the sheet isn't free to run it does get very difficult about 2/3 of the way up. Good luck!