i'm thinking the same - i can do just about everything from the cockpit i need to except for main halyard work. Running a single line back shouldn't be too bad. I need to find a winch for the cabin top, a clean block, fair leads or blocks, and figure out how to mount a block at the foot of the mast to route back. I think the halyard on there has enough length to allow this to happen but not certain. if not i'll pull another through with an extra ten feet. Problem is the cabin top is two heights, so the mast routing back has to be mounted about a foot off the mast step to accomplish the redirection. I'll take pictures and i'm open to suggestions how to manage it.It's already been said, but I'll say it again … point the boat into the wind when raising the mainsail! There is no reason to rely so much on winching the sail up with your small sail. Use the winch handle only at the end to pull the stretch out of the halyard. You will need to develop better technique to avoid losing that handle. Imagine doing this on Lake Michigan with the boat bouncing far more in waves.
I always argue that halyards should be led to the cockpit on a small boat. Think how easily your girlfriend could be tossed into the water if there is any kind of wave action. Small rounded coach roofs are not a good place to stand when you need to use 2 hands for raising a sail. I would consider leading lines aft and standing in the cockpit. You will probably spend more on lost winch handles (that you won't lose if you are in the cockpit) than it will cost to purchase the equipment to lead halyards back to the cockpit.
Even with it routed back, when it comes to being time to pulling the sail down and flaking i'm not sure how that would be possible without going up on the cabin top.
I was also going to get a jack line set up - two of my preservers are offshore rated and have double rings to clip in. shouldn't be too bad to get something set up to permit cabin top walking.
pointing to the wind proved to be ... i dunno. challenging. I had power boats zooming past me on either side and so the notion of pulling a 180 to pull up the sails and then a 180 to get back on my route in such traffic shied me away from it. i left the motor on and keep the wind behind me to get it done. I also had trouble cutting across returning traffic to return to the marina and finally just had to jump through an opening. even no wake they were zipping along from the mouth to lake michigan and i just had to get bold to finally get it home.
if waves are 2 ft or less on lake mich i'll probably just go out there from now on as i got a little shy at the tiller with the room i had to work with otherwise. i felt very cramped and had to be hyper vigilant for not only crew on board but also traffic.
to be perfectly honest, i didn't enjoy the first sail until i was safely back in the dock. right of way was very haiti traffic law. He who's boldest goes first. but i refuse to stay in the dock scared.