Agreed - use a dry film lube on the mast track - McLube or silicone spray. Before doing that, it would even be a good idea to clean the track with a power washer.
If you have an all-aluminum mast with the flapper, remove the flapper. Also read the FAQ regarding raising and lowering the mainsail and do a search on the forum. This topic has been discussed numerous times. There are some tricks to getting the system to work that are not intuitive. Once you know what to do, it works fairly dependably.
As far as lowering the mast with the mainsail attached - very bad idea. You are seriously asking for trouble doing that, especially if there's any appreciable wind. It would be very easy for the rig to get away from you with the sail still up. In the future, if you're unable to get the mainsail down, flip the boat on it's side (with the mast up) and unhook the mainsail. Then flip the boat back upright and pull the sail down. Then lower the mast normally. This is a much safer way to disconnect a stubborn halyard ring.
You can leave the jib on the forestay. If you have a cover, it'll be ok for a while. But the sail will definitely take some abuse this way. Most people remove the jib from the boat when trailering.
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