Daniel, when is the last time you cleaned out your mast track? If the mast had been sitting on a trailer for a while, it will be full of...stuff...that will add drag when you raise the main. Next time you have the mast down, take a high pressure nozzel on a garden hose and spray the track well, top to bottom, use soap and a brush if you have one, but get it as clean as possible.

When it's dry, spray the entire length of the inside of the track with silcone dry lube. Then go spray the luff rope on your main with the same stuff. That should help reduce any drag so your main should slide up easily.

Re. the ring hooking to the hook at the masthead, if you pull down on the main with one hand, while slowly releasing the halyrad tension, the ring will hook on easier. I find mine always needs a little down pull on the main to get the ring onto the hook.

To get it down, just raise the ring (pull the halyard tight, so the ring is up and off the hook) then rotate the mast 90 degrees to one side or the other, and then, after the mast is rotated, release the tension on the halyard and pull down on the sail, while holding the mast 90 degrees to one side or the other of center.

It's all a lot easier when the mast track is clean and lubed up, and the mainsail bolt rope is also lubed up, so the main slides up easily.