OK, I now get what you reported.  Sorry for reading sloppily before.

Confirmed that failing silently is not good.  However I have no idea how
to fix that sensefully.  You might report this upstream, and notify this
bug here. (I didn't find any existing bugs for this, please check.)

To reproduce the general issue ("fails silently") I triggered a failure
here by uninstalling wine32-development, and then trying to start a
32-bit app from nautilus.

However I couldn't reproduce your specific issue here:

I did:
$ cp /usr/share/doc/wine-development/examples/wine.desktop 
~/.local/share/applications/
$ update-desktop-database ~/.local/share/applications/
$ winecfg
--> in tab "Drives" remove drive Z:, so only C: is still listed.
Open file browser (nautilus)
- right-click an exe that is in my home folder, but not in ~/.wine
- "Open with Wine Windows Program Loader"
--> works here.

** Also affects: wine (Ubuntu)
   Importance: Undecided
       Status: New

** Changed in: wine (Ubuntu)
       Status: New => Confirmed

** Changed in: wine-development (Ubuntu)
       Status: Invalid => Confirmed

** Summary changed:

- Wine doesn't run programs from nautilus
+ Wine fails *silently* if running programs from nautilus fails

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https://bugs.launchpad.net/bugs/1658884

Title:
  Wine fails *silently* if running programs from nautilus fails

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