Through tests with the F-14 and F/A-18, I believe that Jester (and/or Iceman) breaks DCS replays.
I will start by saying that, obviously, replays generally in DCS are quite buggy - no need to reiterate that.
However, this appears especially true for the F-14B.
I have run simple missions (for example, the Heatblur F-14B Caucasus Case I) about a dozen times in singleplayer, and the replays do not work for any of them - even when no time manipulation (e.g. speed up, pause, slow down) is done.
By comparison, such replays for simple missions with the F/A-18C work FLAWLESSLY.
So, why Jester/Iceman?
When I run such a simple mission on a server and obtain the server track, the replay works FLAWLESSLY - just as with the F/A-18C tracks. Jester/client data is not present in the server track (evidenced by no F1/cockpit view of the aircraft on a server track).
To conclude: F/A-18C client and server tracks appear to work with simple/short missions, whereas only F-14B server tracks work. I believe this strongly points to Jester data breaking client tracks.