From what people hear about MacGregor 26's, Dyneema could be overkill. Would still work, though.
I concur, Dyneema is, IMHO, a poor choice. It's completely overkill for the forces involved, making it needlessly expensive.
And while it's much (MUCH) easier to splice an eye in the end than conventional double braid, the "fat" portion is also much much longer, which sometimes causes problems.
Mostly though, it's not as nice to "handle" as conventional line; the added "slipperyness" is just never a good thing.
Let me give you two things to think about.
1. Consider so called "regatta" braid. It's made out of conventional material, so it handles nicely. Actually, it handles nicer than double-braid because it just refuses to hockle; bundling it up "wrong" (i.e., no figure 8 loops)
isn't a problem.
And because it's hollow, spicing eyes are again trivial. But because it's not insanely slippery, you don't need a 48x bury; a short bury and a bit of sewing (belt and suspenders philosophy) and you're done.
2. Consider no tackle inside the boom, save for a pulley at either end. Run the line out the front of the boom, down to another pulley and back to the cockpit. At the cockpit, you can have a cleat or a jammer AND use a winch (if there's one handy.
If you're clever and careful, there should be no real change in outhaul tension as the boom swings from side to side. (This IS something to consider in the planning, though.)
For the record, I did exactly this on my 28' boat. I had a fancy (or so I thought) internal arrangement that caused nothing but grief, so I now run a single line out the front, down and back. I'm not sure I've ever used the winch to tension it though.
And should I need (or want) to play with tension, I can do so without leaving the tiller.
(I have this thing about the safety of the cockpit. You never forget going for an unplanned swim in the middle of the Pacific ...)
Hope this helps.
Alan