Do you stay until the end of the conversation or do you leave before it finishes?
Both paths were tested extensively. One tester had a persistent crash that occurred when he entered the Temple District, but starting over with a clean installation solved that issue. Any time you reinstall mods, there's a chance of file corruption, and cutscenes tend to be very sensitive to this.
Yes I stay till the end just after I tell him goodbye and I'll meet him later at the temple of Oghma the game crashes.