OK - try skipping that package.

Okay, I'll install;

Install wine on a 64-bit architecture (with i386 as foreign 32-bit architecture)

and

Install wine-development on a 64-bit architecture (with i386 as foreign 32-bit architecture)


should I do both?

I did the first one so far and noticed this;

Warning: The home dir /run/uuidd you specified can't be accessed: No such file or directory
Adding system user `uuidd' (UID 117) ...
Adding new user `uuidd' (UID 117) with group `uuidd' ...
Not creating home directory `/run/uuidd'.



Does that mean anything?

I have read (quickly, scanning the Debian wiki ..) that it is preferable to install both wine and wine-development on Debian. So yes, I would go ahead and do both.

This is extremely odd. I am at a loss as to how to explain this. Perhaps more experienced Debian users here can help.

Did the installation otherwise finish correctly ?

Yes, it did and so I had to run the exe like - wine /root/Downloaded/Program.exe and went through, wrong installation directory like Program Files instead of Program Files (x86) but whatever and when I try and run the program it doesn't do anything, lots of weird messages in the command window but can't get that right now because unable to type on the system now so am rebootingm but looks as though that process has failed :(

Again, it sounds a lot like what happens when trying to run a program on Wine that is not compatible with it.

Some hints:

- Make sure you are running the appropriate architecture (32 or 64 bit). This can be set individually for each WINEPREFIX with the WINEARCH attribute.

- At times, some programs require the Microsoft .NET framework instead of Wine's own Mono. A version of this can be installed with winetricks.

- Sometimes, installation of a program under Wine requires that the version it is emulating be set to a particular value (example, Windows XP) for it to function. Sometimes this version can then be set to something else to actually run the program. This can be set in winecfg.

When I run winecfg, I get this;

wine client error:0: version mismatch 457/447.
Your wine binary was not upgraded correctly,
or you have an older one somewhere in your PATH.
Or maybe the wrong wineserver is still running?


When I tried to install the program.exe with just wine it installed Mono and when I tried to run the program.exe install with wine-development it installed .Net

... Come to think of it, when you say you expected the install to use Program Files (x86) but it used Program Files instead, it makes me think you may be trying to install a 32-bit Windows app in a 64-bit Wine environment. Could this be the case ?

... For this stuff, I must admit I've never seen anything of the sort ... It almost looks like it's complaining about having more than one version of Wine installed ...

I'm not sure. It installs fine on my Windows 64bit computer.

Is there a command to purge all versions of wine and it's dependencies?

I only installed wine and wine-development

Okay, I seem to have it working now with this guide;
https://wiki.winehq.org/Debian

I only thing I can think of that I did different this time what I ran apt-get upgrade after doing an apt-get update like in your previous post. Could this have fixed something on my system?

It could have - that will just make sure you have the most recent versions of your installed packages. Cool that it worked out in the end.

Sorry I couldn't be of more accurate assistance, I'm afraid I underestimated how my lack of familiarity with Debian would hinder my success at troubleshooting this with you.

Good show getting it done yourself, though !

Cheers and don't hesitate to return - there are many experienced Debian users here.