Elsie -
The reality is that you will be having hands off the wheel while using the winch. I imagine that the first use of the DRILL will be raising the sail with the halyard (with a different winch). You’ll, then. have to move the drill to the Anderson. Do you use an autopilot ?? I ask because you must leave the wheel to raise the sail. Are you motoring along when you raise the sail ??
OK - let’s (sort of) go back. One way or t’other, let’s say that the sail is raised. So you hand pull the MAINSHEET (fast and easy, hand over hand) until it starts to get tough. You insert the drill and va-ROOM. The mainsheet tightens right up. Back to the wheel you go.
Presently, you still cannot steer at the same time that you are using the existing mainsheet winch, right ?? Though I’m not REALLY sure why, if it’s vital to keep the winch close to the wheel, well, so be it. Otherwise, mount it further forward making CERTAIN that the handle will not be encumbered by the dodger frame or anything else AND the coaming will be a titch wider. Furthermore, mount it so the self-tailer points directly into the cockpit (same direction as in Mark Powers’ photo). The sheet will will end up in the cockpit. Furthermore (once again), the max distance between the two furthest bolt holes will be a little less than if you mount it with the self tailer facing front or back. Maybe a 10% - 15% narrower BOLT footprint (not winch footprint).
John Newell is a VERY experienced sailor who does race his boat. He must have many good reasons for the sheet to tail on the deck. As a purely recreational sailor, I would be scared to death of a good length of sheet falling on to the deck and then, perish the thought, tumbling into the drink and wrapping itself around the prop. Once was enough for me and it was a reefing line, not the mainsheet.
Last point - I’d go with the 28 winch. Basically, it means that on the 34, one crank will pull in more line. IF the winches are truly the same physical size, I kinda think that the smaller winch will be easier to grind (but you’ll get a bit less line pulled in per crank). Or, I’m wrong (it does happen) and, indeed, with NO MORE EFFORT, you be able to crank a little MORE line in with the 34. And, you bet, I’d call Anderson Tech support and ask them.
As I write this, I notice a plethora of other responses and can’t wait to read them !!
Have fun !!
Ernie A. in gusty Toronto.