The Harbor Freight Tools solution
I too am a fairly new Mac 26 owner, a 1993 26S to be exact. There are Macgregor owners out there who (so they say) simply pin the foot of the mast, stand on the pop-top, and lift the mast into place. I'm big and strong, but that stunt is well beyond my abilities, not to mention sure death for my roller furling foil. I chose to use the gin pole and tackle system that came with the boat.My first attempt (while on trailer) nearly did me in, largely because of your problem: I couldn't control the furled headsail and furling drum while I was paying attention to the more important task of mast raising. I also had a little difficulty doing all that winching without bering in the cockpit where I couldn't do anything with the furling system. In any case, I simply needed a better way to rig up if I was going to enjoy sailing the boat.I was poking through a Harbor Freight Tools catalog one evening when a small, 2000 lb. 12VDC winch for only $50 grabbed my attention. It only weighs 16 pounds and has planetary gear reduction, a free-wheeling clutch, 3/16" cable, and a remote raise/lower controller. I figured for fifty bucks I could easily take a chance on whether or not I could adapt it to the mast raising job.I mounted it on three through-deck 5/16" bolts just abaft the strap eye for the Macgregor hoisting system. I tried it out for the first time this morning with great success. It pulled the mast up smoothly without even breathing hard! I stood beside the port bow with the controller in one hand, and tugged the roller furling drum forward with the other as the mast went up. Every so often, I'd stop and walk around the boat to make sure none of the stays had fouled. The winch easily pulled the gin pole down far enough for me to fasten my forestay. A touch on the "Lower" button, and the cable was slack enough to detach. I'm hoping it is clear enough of my headsail's foot that I can keep it in place. If so, I plan to make a padded cover out of coated pack cloth, replace the cable with stainless 7 x 19, and install a power outlet for the controller right near the winch. This will sound like overkill to a lot of purists, but it makes sense to me. When I asked the boat's 65 year-old former owner why he was selling the boat, he told me that he and his wife were too pooped after rigging up to do any sailing. I'm nearly his age and have the same problem. So I am adding every device I can think of to make rigging and sailing convenient. The power winch is the best so far. I plan to submit pictures of the finished installation to macgregorsailors.com in the near future.