I had mine rear pulley replaced at 63K miles on 07 UC but belt was in good shape and yes ESP doesn't cover it.

 

Ive seen the belts go out alot earlier than yours did.
If you can afford it.... Go with the Rear IDS sprocket kit & a Sidecar Belt.
The IDS will get rid of some compenstaor rattle
I recall the Sidecar belt is the strongest HD makes
Double check with the mechanic.....

 

Yep. why loose another year of riding.

 

I'd go with the IDS and a 68 tooth sprocket ......same money, a little better low end performance.

 

What size is the stock Sprocket ?