Antes de executar o wine, altere a variável de ambiente WINEDEBUG, para
alterar quais mensagens são exibidas:

WINEDEBUG=+all
wine ..... (execute o programa)

Veja se o programa não entrou em loop, ou se está apenas demorando para
iniciar.

Segue um trecho do `man wine` que diz sobre isso:
WINEDEBUG
              Turns  debugging  messages on or off. The syntax of the
variable
              is of the form [class][+/-]channel[,[class2][+/-]channel2].

              class is optional and can be one of the  following:  err,
 warn,
              fixme,  or trace.  If class is not specified, all debugging
mes‐
              sages for the specified channel are  turned  on.   Each
 channel
              will  print  messages about a particular component of wine.
 The
              following character can be either + or - to switch the
specified
              channel  on  or  off  respectively.   If  there is no class
part
              before it, a leading + can be omitted. Note that spaces are
 not
              allowed anywhere in the string.

              Examples:

              WINEDEBUG=warn+all
                     will turn on all warning messages (recommended for
debug‐
                     ging).

              WINEDEBUG=warn+dll,+heap
                     will turn on DLL warning messages and all heap
messages.

              WINEDEBUG=fixme-all,warn+cursor,+relay
                     will turn off all FIXME messages, turn on cursor
 warning
                     messages, and turn on all relay messages (API calls).

              WINEDEBUG=relay
                     will  turn  on  all  relay  messages. For more control
on
                     including or excluding functions and dlls from the
 relay
                     trace,     look    into    the
 HKEY_CURRENT_USER\Soft‐
                     ware\Wine\Debug registry key.

              For more information on debugging messages, see the Running
Wine
              chapter of the Wine User Guide
-- 
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