a few issues

[ricks 89]

gotta few issues w/ my baby. 89 ck1500 350, good truck, driven hard.
anyway, now and then on startup, i get a vibration that lasts for a few seconds then goes away, this coupled with the starter not kicking in or kicks in but doesnt engage the flywheel. it always starts the second time ( minor annoyance -for now!)
engine runs fine, usual crappy milage for a v8, but i have to toss it into OD after 45 or i get 6 miles p/g.

anyhow, does anyone concur that the starter is in need of an overhaul or a replacement?
2nd issue- any suggestions as to why it wont shift into overdrive after 40 or 50 mph.