Ryan,
I put a belt drive on my Speedmaster just before the trip to Georgia. I adjusted it in PennsylTuckey on the way down and it hasn't needed anything since then. Over 3000 miles on her so far and so good. By the way, my GF lives on a really nasty backwoods dirt road and so far, knock on my wooden skull, no issues there either.
The belt on the kit is top notch, it's a Goodyear Blackhawk if that means anything to ya. First belt drive I have ever had but I like it so far. Especially yesterday when I finally got around to washing my bike. No muss, no fuss with the rear wheel area now.
Big $$, if you got them to spare I recommend it.