I'm still not certain whether this problem is specific to WINE, but the limited data I've been able to gather suggests that it might be. (Hopefully describing it here will at least be more helpful than Reddit [1].)
In "The Contract" storyline of GTA Online, during the finale mission of the "Nightlife Leak" chapter, the character must take an elevator from the Casino Parking Garage to the Penthouse Floor. Upon entering the elevator, the screen goes dark for the transition as expected. Sometimes a loading spinner starts, sometimes the background crowd noise starts, sometimes it stays completely blank; but regardless the game stops responding and has to be forcibly terminated. It does not write a crash log [2] (as it has in other less-predictable cases), and the debugging logs I know about [3] haven't been written to for minutes (or more) before the freeze.
I've been trying to eliminate variables, but of course there are quite a few to address, and it takes a while to re-launch the game and run the mission. My notes aren't great on the variety of settings that I've tried, but I'll record a few particularly relevant points and follow up if there's more that seems useful.
- One time [4] I was able to get past that point in the mission, but I can't be sure what combination of factors helped, and I haven't been able to recreate them. I believe it was after I had forced a re-download of the entire
update
directory and turned my graphics settings very low. Whatever part of that combination worked, I haven't been able to recreate it. - I downloaded the game through the Epic Games Store; at least one other reporter from Reddit had the same behavior with a Steam download.
- The location being loaded is one that I don't have access to any other way, so I can't personally check whether it's triggered by location alone or in combination with the mission. Others have reported that the relevant area is also part of the Casino Heist and Cayo Perico Heist, and that they've seen the same behavior.
[1] Two posts for reference: (https://www.reddit.com/r/gtaonline/comments/swqay5/what_is_unique_about_the_penthouse_floor_of_the/) and (https://www.reddit.com/r/macgaming/comments/sxfmsz/gta_v_from_epic_store_works_well_still_hunting/).
[2] Path where I've found crash logs in other cases: drive_c/users/crossover/Local Settings/Application Data/Rockstar Games/GTAV/CrashLogs/
[3] Filenames in my collection of other logs: GTA5_d3d11.log, GTA5_d3d10.log, Launcher_d3d11.log, Launcher_d3d10.log, SocialClubHelper_d3d11.log, DirectX.log, launcher.log, prelauncher.log, socialclub_launcher.log, socialclub.log
[4] Honestly, that might be more frustrating than if it had never worked. But at least it tells me that the data isn't inherently corrupted upstream or something.