I am working on a 1995 Road King that has a problem with the starter jackshaft not engaging every time. It appears to be riding on top of teeth on basket. While inspecting the coupling and pinion gear bushings I've decided to replace them. My question is "Am I overlooking anything?"

 

possible bent jackshaft?

 

Bushing wear is likely given the year - at 20 a lot can happen. Other things to check are clean and solid battery cables, corrosion in the fuse block, worn ring gear teeth.
This assumes the battery is charged fully. If there's a relay involved it'd be another possibility.

Luck