does anyone have any ideas what could lead to this problem?
you have a alignment bar and did not use it?
not a triangle. and what rubber pads!
Remove the orings from the shaft and yes it should slip in all by hand unlike my sea ray. If it slides in all the way by hand, pull back off and put the o-rings back on. From what I gather here, new o-rings can make it hard to get in all the way even when lubed properly.
I also assumed you greased the splines right?