I went one tooth bigger on my 98 FXSTC but its an EVO. I have an S&S carb w/ K&N air cleaner, SE203 cam, SE easy install push rods, SE roller lifters, V&H straight shots and rejetted carb. With this combo I have plenty of power on the low end and could still use a little more gear on the top end. I don't have a tach so I have no ideal what RPMs I'm turning but I can run 75 without to much discomfort.

 

So that took you to a 35 tooth I guess. Yeah the convention is a 34T I've seen mostly. Your bike can definitely handle it. My old '90 was a beater with a top end rebuild to 10:1 compression.. It had no problem with the 34T pulley.

After considering the costs, I'll probably go the 34T Andrews route vs a 6-er.

On the Baker DD6 there's some heated discussion but it's basically a similar system to the stock H-D 6 speed.
They get the RPM's lowered not by the 1:1 final gear but instead by the compensator sprocket size increase (I think).
The OD6 Baker Kit would probably be my choice if I went that route.. It's apparantly bulletproof.

But holy moly.. Ch-Ching! $$$$ I can't justify looking at the transmission on my bike (about the size of a football) and looking over at my John Deere, and knowing just modding the tranny cost as much as my LT180 lawn tractor.. Just the part is $2 grand!

I'll have the techs do the sprocket when they do the 10K.