Just got back from just under two months in the San Juan Islands (WA) where I sailed my Hunter 27 quite a bit by myself and sometimes with guests on board. I have been using the WinchRite for almost three years now (since it was first on the market) and I have to say that without the WinchRite I wouldn't be sailing anymore.
Yes, we had our problems at the beginning. Although my Hunter 27 was brand new the main sail were not cut properly and was difficult to winch out. Doyle recut the sail and it pulls out much easier now. I've had over ten years with furling mains and you should not have to work to get the sail out--something is wrong. My WinchRite has an easy time with furling and unfurling.
I've also used the WinchRite to unfurl the jib although it is a small one. It just makes sailing so much easier. And, yes, I have seen the Milwaukee drill but quite frankly it is too heavy for my wife to use and I want her to have fun sailing as well.
To Jim whose WinchRite didn't have enough power--I'm sorry you didn't send it back to the company to have them check it out. My WinchRite has plenty of power.
My wife and I are approaching our eighties and still want to sail. The WinchRite does the job for us.