Two questions:
1. What condition is the flexplate in? The teeth on mine were pretty chewed up... while I had my engine out I replaced it.
2. You're on the stock type of starter... that is, a one wire (moving pole) starter, not a PMGR with a separate solenoid wire?
The original Moving-pole type starters can be rough on starter teeth as the motor spins while the gear is slid into place (or so I've read). The PMGR of the 1990's fixed this among other improvements (faster cranking, less battery demand, etc.)... one reason why it's a common swap (other than replacing the starter for the newer unit, all one does is move the existing starter cable to battery hot, and add a 12 gauge wire from the solenoid output to the motor's solenoid).
1984 F150: 300 L6, AOD, RWD. EEC IV / TFI, Feedback Carter YFA Carb. Stock everything but radio (for now).