I'm not sure if I understand what your issue is but if I am correctly understanding, what I would try is setting up a virtual desktop in Wine. You can do this by running winecfg in a terminal to open Wine's configuration application, add GTA 2's executable to the applications tab, select it so that you are only changing settings for GTA 2 and not everything, then go to the graphics tab, select emulate a virtual desktop and set the desktop size to the resolution you want.
Not sure. You could try running it in Valve's gamescope compositor. Maybe the game only supports that low resolution
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