Something to watch. I have never raised or lowered the mast with the trailer winch,only cabin top winch.
In the pic the mast has just been raised. You can see the ginny pole needs to be around 300mm longer to make sure the raising line always goes in when lowering. If it does not go in when lowering, the mast will come down much quicker than expected.
In my case I use the extra fitting I have put in the foredeck to attach my cruising jib furler to pull on to raise the mast. This fitting is 250mm behind the forestay attachment point. Others may need the ginny pole even longer as they will be pulling from further fwd. In the pic the crusing jib is rolled up on the fore deck without the furler. I like the cruising jib on a continuous line furler but it does tend to pull the forestay in when furling. I have a plan to stop this which I will post once tested.