I like the whisker pole.
As for the rubber self-tailing thingys, they are called winchers I believe, some swear by them others say don't waste your money. I think they work ok under light loads but they are not cheap if I recall.
I have horn cleats after the winch but I don't tie it off, I just wrap the line under itself, 'jam' as it were, for a quick release.
One our club members had them on his O'Day 25 and I think they got old and delapidated. Those rubber spreader boots get the way after a while and they are pretty pricey too. I made my own spreader boots out of leather back in 2007 and they're just as good today as the day I made them.
You probably have the jam type horn cleats like the one I installed on my boat for my furler control line this past spring. Wayne has them on his Seaward 22 and he was using them for his sheets before he installed the open clam cleats like I have. He left these cleats on his combing and he uses them now to snub off his boom brake control line. He built a copy of the Dutchman boom brake a couple of years ago and was using that for a while until he found out that the same thing could be accomplished with a Black Diamond mountain climbing "Super Eight" belay device. I bought one for my boat that I hope to install next year.
I like that horn jam cleat that I mounted for my furler line. I didn't realize it at the time, but those cleats need to be mounted on an angle from the sheet coming off the winch, or they won't work. I had to mount my cleat straight with the combing because I didn't have enought room to mount it on the required angle. Luckily it will only work if I wrap the control line around the cleat clockwise.
I love my whisker pole. I should have sprung for one years ago but I just didn't want to lay out the money back then. I kept my eye out for one at the marine consignment shops but the ones I saw were always built for boats smaller than mine.
I'd like to pick up a snap type extrusion for my whisker pole and replace that prong. Then I could attach it to my Gennie sheet.
Last summer Penny and I were sailing back from Bristol RI and we were on a course down wind heading back toward Fall River Ma on Mount Hope Bay when it started to rain. I quickly dropped the main and covered it. After I poled out the Gennie, I tied my 8'x10' polytarp over the boom to the lifelines and also tied two more smaller polytarps over the cockpit and we were nice and dry about six miles all the way back to the club. We probably looked real funny out there but we were nice and dry. Man, do I love that whisker pole!