Your bendix is doing exactly what it's supposed to do, there's no reason for the gear to rise up the shaft if it's spinning at the same speed as the shaft, in fact the spring will keep it pushed down.
Sounds like your getting an initial half hearted pop but then the motor is not continuing to run.
Has it ever worked for you trouble free in the water?
Is this something new that has started happening?
Sounds like flooding combined with the extra back pressure to me.
You are right. I get a very weak chug, for a tenth of a second and then the starter gear continues to spin as it disconnects from the motor. If it would just stay connected for another second it would fire. The motor tries to fire immediately at all times. Aside from this issue it is the fastest starting outboard I've ever had.