So I just took my starter off to get ready for the LTs, now I'm curious as to how or if the starter drive gear keeps its tooth alignment with the flywheel...
Does the drive gear mesh immediately when it comes out, or does it hit the flywheel, spin, and mesh after spinning?

Just curious...

 

It meshes first if it is working correctly. The design of the solenoid and mechanism is such that the motor gets no power until the gear is extended.

On the older "Bendix" style starter drives, the motor starts first and then the gear is pushed out by inertia and a helical shaft on the gear.