Sounds like the starter drive (sometimes improperly referred to as "bendix") is not sliding on the shaft to engage the flywheel. I would remove the starter and do a bench test to see if that is the case. You certainly want to remove the starter and inspect before doing any damage if there is an alignment issue.
CUSTOM WHEEL & TIRE PACKAGES
$125 LED LIGHT PACKAGE - FREE SHIPPING
REBUILDING HOLLEY MARINE CARBURETORS - $249 DELIVERED
Email - email@example.com