Most problems with getting into gear on the 9.9 and 15 are because the connector between the two sections of the shift rod was not replaced correctly. It is necessary to completely remove the screw in order to catch the recessed area at the end of each section of shift rod.
The shift rod on this 9.9 comes up through the top of the cowling and looks ok,. I took the shift roller off and it seemed to work ok. I noticed the threads that hold the bolt and roller on were stripped and wouldn't hold it solid. Maybe it was preventing smooth shifting. I'll let you know what happens. I may just epoxy it in. Thanks.