We sail our Catalina 42 on the Columbia River and except when we head north or south offshore it is all short-tacking. Our small club concentrates on cruising but once a year we hold a casual "Race Cruise" in late May. It is normally a little or no wind drift party but a couple of years ago it surprised us all with summer like conditions which is 15-20 kts of wind right up the river (the course is downriver, naturally) With my wife helming and me doing all the grunt work we logged 24 tacks in 75 minutes. At the end I figured I had maybe one more tack in me IF it were necessary to save the boat and crew. Otherwise I was one Spent Cartridge!

We find we are sailing a bit less as the years add up although I am lucky in the fitness/infirmaties department. My winches are 1990 vintage so cannot be converted and new electrics are not in our budget. If we could convert the primaries I would do it in an instant. I do use the right-angle drill method but consider it to be a second-rate solution. It doesn't have enough power to make the last couple of drum turns under full summer time conditions.

I am almost embarassed to ask if you have checked with the Catalina 36 organization. I have dropped in there on occasion and they are an active group with a huge membership for a single model. I should imagine that someone there has done exactly what you describe.