I am replacing my tired 80" with an S&S 88" and am looking for some feedback on other builds. This is what I am doing:
Breathing the heads
10:1 pistons (not sure of the clearances just yet)
Sportster rocker covers
It is a 2002 motor and I have not heard if there was an Achilles heal to this year.

 

Forgot to mention the Woods 6 cam.

 

Why? Slap the wheels in a set of ultima cases, and throw on some 3-13/16th cylinders along with a fat *** andrews cam. 97" and rev to the motha ****in mOOOOOOOOOOOOOOOn!!!!

 

Here is another thing. Do you even ride hard enough to make use a big bore kit? A bigger bore is going to increase your usable RPM's, but with the cam you'll need to make a big bore kit work, it's going to move your power band way up in the RPM's. If you're just a cruiser, never get over like, 4800, you'll be better off with a stroker, whether its 89" or bigger with more bore. The sky is the limit and the cookie cutter sizes aren't something you have to go with. I have plans on a 105" with a 4 5/8th stroke, 3-13/16th bore, 12.5:1, leineweber E8, big fat carb.

 

Now that should get you to the moon!! This bike has been my bread and butter for the last 6 years and reliability is in there with a little added performance. Cookie cutter is fine if it is proven to be reliable. I don't have time to be wrenchin. I do that all day at work. I cruise, but when it's time to get it, I want it there.

 

Well, then if you're just a "cruiser" I wouldn't be doing any big bore kits. I ride the **** out of my ****, constantly banging off the rev limiter... I can use a big bore kit. I would recommend slapping a set of S&S 89" flywheels into your stock cases with appropriate head work and a nice cam; keep the compression mild. Will do everything you could ever want.

 

Part of the deal is trading the 80" as part of payment so my wanting to build it up is not going to happen. It is 24 years old and tired. Some freshening up and it should roll another 120,000, but I'm not getting any younger and have a chance to bust loose one last time. Of course, as Clint said, "Every man must know his limitations".