Mercury outboard question

I tried the wiggle/jiggle and it wasnt working. Had lwr unit off and on more than 15-20 times. Just wouldn't go. Watched Boobtube and turning flywheel a tooth or 2 was mentioned. Finally dropped in. I'll add oil today and chk if my back agrees.
Thanks all.

I had a bit of an issue with the spline engagement on that Chrysler as well. The spline ends, although tapered, had all sharp corners / edges. I stoned the sharpies off and it still wasn't a cakewalk to engage.