I have not tried it. Before I set up my tiller pilot (which has really made me lazy, btw) when I wanted to go forward for some reason I would tie the tiller slightly to windward, check that she was balanced, and then go. Frequently the boat would sail by herself for hours in that condition, oscillating between two and three degrees on either side of my desired course, and I could get all sorts of stuff done. As a result I now have a favorite jib. But if I'm using any other than the favorite jib, or the winds are too light or too strong, it will only last a minute, sometimes less, before she rounds up.
A tiller lock or comb would give you the same benefit, plus prevent the tiller from falling all the way to windward (which sometimes happens to me and makes doing this stuff on a reach sort of dangerous).
I am luck in that the PO ran halyards to the cockpit, so for hoisting and dousing I only need to go to the foredeck to secure or untie the sail. With just the mainsail up, the boat will fall off in light winds or round up in strong winds pretty quickly, so if you wanted to use this method for hoisting/dousing the jib, you wouldn't have much time. I expect it would be the same if you used your mainsheet in some clever way, maybe a bit better. But I expect it would take so much time to set up that it's not worth it for just a quick run to the mast.
Are your halyards external? If so it should be fairly easy to mount a block somewhere and run your jib halyard to the cockpit. Not sure how big your boat is but you probably don't need a winch to get the jib up... after you're set up, you can always add tension at the mast later.
1972 Catalina 27