https://bugs.winehq.org/show_bug.cgi?id=56087
--- Comment #10 from Rafał Mużyło galtgendo@o2.pl --- ...yet the early warnings make me wonder: is wine-mono properly installed in the prefix ?
Also, that cdcheck might be as simple as a check for drive label. In that case, perhaps identifying the mount point as a drive in winecfg and setting its label could works ?
Though WINEDEBUG=file might offer hints as to why that "Setup is unable to find a required file: SIERRA.INF" error is the initial reaction...