Using a device to help in lifting the mast is all about angles, the greater the angle the easier the lift with the device.
Using the trailer winch you will need someone lifting the mast to the 30 degree angle to allow the trailer winch to take over, if you can get the winch cable to pull at the top of the mast at a 30 degree angle no one would need to start the lift, which means the cable would have to go over the top of a tower above the winch to create the angle, and then you still have the catching of the cables up on deck. Without the angle of lift on the winch cable two fellows are needed and if strong enough they could lift the mast into place without all the setup of using the winch. Look up gin pole or A-frame on youtube.
Three more ideas;
1.5 people, yourself and a teen or wife. Using a 100 foot line attached to the forestay and stretched out in front of your tow vehicle about 4 more car lengths, a teen or wife can hold the mast after you make the cockpit lift. At this angle of the lift one or the other can pull the mast up very easy after you clear all the shrouds on deck.
Yourself only. With practice I have attached a line to the forestay and run it through the hole in the mooring bow cleat and lay the line on the cabin top. Lift the mast in the cockpit and when I get to the cabin hold the mast with one hand and grab the line on the cabin top and pull it tight and then in one quick move let go of the mast and hold onto the line with both hands and then cleat it off on top of the cabin top. Clear the cables and then finish the lift from the cabin top, I was much younger and stronger when I did this.
I now use what I call a double mast crutch system, the second crutch is placed on the cabin floor in the hatch way and is just the right height to lift the mast in the cockpit and when I get to the cabin set the mast into the second crutch. This holds the mast at the right height to clear the cables and lift the mast from the cabin top by myself when I was younger and stronger. Now, no one has to hold the mast part way up while I clear the cables on deck, and with help finish the lift from the cabin top.
A lot of this has to do with your own ideas and capabilities, after you lift this mast a dozen times ideas will start to flow, just make sure you have help the first couple times you try something, you could injure yourself or do lots of damage to the boat!