Motorcycle Repair: repair starter on 2000 heritage, spark plug wires, heritage softail classic

Question
I have a 2000 heritage softail classic. When I try to start it the starter spins but it does not engage the pinion. Then there are other times it will engage and start.

Answer
Drain the oil out of the primary and remove the derby cover. Check the gear that the jckshaft runs on for damage. Remove the spark plug wires, so the bike doesn not start, and bump the starter. Does the jackshaft come out and hot the starter gear on the clutch?
Mike