Chances are it is NOT the belt! I had over a 100,000 miles on my 08 belt when I swapped it out and my original belt didn't have any cracks or break and it wasn't stretched.
In most cases a bad bearing in the primary will show up as a oil leak first because the bearing seal is going out.
There is a bearing in the rear pulley and it can go bad, I had to replace 3 rear pulley bearing on my bike. I would lift the rear wheel off the ground and rotate the wheel back and forth and see if you hear a noise that may be bearing related, you can also grab the rear pulley and see if there is any in/out movement which would indicate pulley bearing failure.
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08 FLTR candy red sunglo,with 2015 103 HO, V&H Dresser Duals with Monster Rounds, Power Vision tuner, Willy Shiny Wheels and Forks and a bunch of other stuff.