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At first the launcher crashed when selecting video settings with an "Method not found: 'Int32 System.Runtime.InteropServices.Marshal.SizeOf" error, but I was able to fix it by installing dotnet46 using winetricks (be advised that dotnet45 or dotnet452 are too old).
However, even after doing all that the first game crashes after the Aksys Games logo with "An application error occurred! "Nine Hours, Nine Persons, Nine Doors" was termed." error. The second game just freezes on a black screen after some logos. Judging from other threads, this problem doesn't seem to be unique to wine, though. I'm still hoping this can be fixed with some more overrides.
UPDATE: I was able to get it going a bit further by installing ffdshow. It now displays the title screen, but crashes immediately after selecting Start,
I truly hope there is a Mac port, if anyone manages to work out 999, please offer a solution!
It gets better: I installed LAVFilters 0.69 from here[github.com] as recommended by someone on reddit. And now I have the VLR opening video playing, but with no audio. So close :) Apart from that the game seems to be running fine.
Even better: for curiosity's sake I tried 999 again after installing those codecs... and it didn't crash on me after clicking Options or Start. The sound was muted for some reason, so I had to fixed that in the options. But after that... the game plays just fine. It suffers from missing audio in the opening cutscene like VLR, but now we're getting somewhere!
Hopefully the missing cutscene audio can be fixed by fiddling a bit more with the codecs. So yeah, this is very playable after some fiddling.
Also, regarding lavfilter- when I download it and then run it, it immediately gives me the option to uninstall it and doesn't actually run. Any tips?
i only use wine for decade old games, the last thing i want to do is give windows another extra sale.