The faces.dat file in an OOTP save contains information about player's faces, and along with the /jerseys and /ballcaps images are used to generate players pictures. Any GM should be able to generate pictures locally with those 3 elements.
Unintended mishandling of files could end with faces.dat missing players and as a consecuence not allowing other GMs to actually do it. Issues specifically arise if there are multiple commissioners running sims, not including faces.dat, and also sharing player picture image files outside of OOTP, like via ZIP files.
Newly created player pictures, like when a player changes teams during a sim, are included in one (and only one) league file, if you have "Include New and Changed Images" set in the League File Settings.
Using "force update" generates new pictures files on "league.lg\news\html\images\person_pictures" and also adds data to faces.dat when you exit the file. However, using this option does not generate new pictures or updates faces.dat if you have png files for that player already in "person_pictures".
A commissioner having pictures already in "person_pictures" paired with an incomplete faces.dat will end up with issues related to player pictures in game, for themselves and GMs.
Per above, new images can (and should be) be included in a league file, however, the game will delete these pictures and replace with generic ones if you try to view one of these players in game, and the player information is not in faces.dat.
To get fully updated pictures and faces.dat containing all the players in the league for which pictures are enabled is:
It would be a good idea to do this once or twice a season, like on Opening Day, and shortly after the draft is imported would be good times.
A further recommendation is to create a zip file containing the league caps and jerseys to share with GMs, which they can put in their league.lg folder to have the necessary local files.
Force Update for player pictures
League Upload Setting for New and Changed Images