Yes, no, maybe on the compression thing with cast pistons.

Hence would check piston rod top bronze bushings to wrist pins, if the rod bushings need to be replaced if too much slop, lathe the factory gaskets off the base of the jugs to start with since only take a few mins that way, get the jugs bored next size up, pick up the new pistons, rings. gasket set, then dry fit the jugs to base with new gasket, new pistons in place with just jugs bolted down tight, and see what squish you have from top of piston all the way up, to top of jug, then add in the thickness of the head gasket in play.
Ideal will be .030", and if you have a larger number than this, than can face the bottom of the jugs back in the lathe to get the .030" squish. I would not go less than this if the plan is to run on stock pump gas, since higher compression could be need to run higher that what you can find for octane pump gas, plus the whole starter problem with high compression and no compression releases on the cylinder as well.
Note, if your plan was to go high compression, then really need to change out the piston rods to forges as well.

As for heads, break them down and take a good look at the seats and valve faces for rust pitting. Sometimes you can save the valves, while most of the time with valve and guide wear, new guides from the old one worn too much, valves, springs, with the seats re-cut to remove any pitting problems on them. Hence the pitting problem is more of the amount of time bike sat no ridden, where moisture got to both surfaces to cause rust pitting over time itself.

Also, with top end off, good time to check the lifters, the cam lob surfaces for case hardening worn off the lobs, change out the cam bearing, and such as well.

 

My bike blew up because of cast (stock) pistons. Go with forged. They are stronger.

carl

 

You have cast pistons now at 100,000 miles the original design is for long lasting cast - be careful changing what really worked

 

What model and year bike is it??

 

‘97 Road King

 

I had a friend of mine that had a 94 road King and he bumped up the compression a little bit and put in a V-Sunder EVL 3010 cam and I got to tell you I was really impressed with that at 9.5:1. I know a couple guys had said stick with the cast but if you're going to do it might as well go with the forge pistons that's just my opinion.. I know that's exactly what I would do that's all..

 

The combination you had lasted 100k miles, I would be think hard about changing a proven setup. Go fast stuff becomes a rabbit hole and the word "reliability" is not usually found in said hole. Good luck.

 

Question, since when was the skirt coating applied to OEM cast pistons??

 

This one was built in November of 1996

 

Seen far more galled up expensive forged pistons than I have cast in low mile motors.