Replying to my reply, because why not?
Got everything back together. Took my dremel to the inside of the end case and shaved about half a millimeter off all around. Bearing fit after that. Put it back on the bike, filled her up with oil and she came to life on the first crank with no effort.
Warned her up for a good ten minutes and shut it down. Waited ten seconds and tried to start back up - this is usually where I end up endlessly cranking until my battery runs down...not this time, started up first crank again!
Finally I went for a ride, couple miles to get things really warned up. Got home, shut down, started right back up first crank! I think I can safely say my hot start problem is completely gone.
'92 Kawasaki Vulcan 750
Rattle-can high gloss black paint job
Frame, engine, Headers/exhaust painted satin black
Ears shaved, K&N pod filters
TPE Stator, MOSFET R/R, Magna Power AGM battery
Pickup Coil mod
New mirrors, grips, cables
Straight pipes with 8" baffles