I really like this idea. Many people who are new to Linux don't know that you can run quite a few Windows applications under WINE. Other people who are new to Linux don't know that you can't run Windows applications natively under Linux. Also, people who are experienced with Linux have often been frustrated by WINE in the past, not knowing that it has improved much recently. As long as the dialog box includes a warning that many Windows applications don't run well under WINE or don't run at all, I think this is one of the best ideas I've seen yet.
I like the idea of explaining to the user that the use of wine is at their own risk and that the application in question could be harmful to their systems.
The last thing we need is people blindly clicking exe's in Linux.
A pity this isn't this done in general. I guess EXEs are the most obvious. Other filetypes e.g. mp3s will be associated with applications which require installed codecs, not the codec themself, so the application runs it's the application that offers codec installation.
This is also a bad idea if the user mounts their windows partition and blindly clicks on program files - I think you're supposed to install individual programs to WINE instead.
My impressions is that wine installation under Ubuntu isn't sufficiently well supported to justify automated installation. But I would like to see a message which suggests WINE. I think it should include a link to some documentation, e.g. the wine application compatability database, so you can make an informed decision on whether it's worth trying.
I understand and agree, that Users coming from windows should have an easy transition. But the suggestion to install Wine would go too far IMO. Wine is just an emergency Solution. GNU/Linux is GNU/Linux and Windows is Windows. We shouldn't devaluate Ubuntu. We should be Proud of our Repositories. There are Things, that are sacred. We shouldn't dilute the Meanings of those sacred things that make GNU/Linux so powerfull. Using the same Keyboard Shortcuts as in Windows, or arrange the Menu's in a similar way is perfectly ok. But make the Transitors (correct english? XD) think it's perfectly fine to execute .exe's with a GNU/Linux isn't.
A message *suggesting* Wine as a possible way to run the .exe is a very good idea!
But it should *not* be installed as automatically! (Not like MP3 support etc.)
When offering to install MP3 support we *know* that the .mp3 file will play. In constrast with a .exe file there is a *possibility* that it might run ok in Wine. But for a random .exe file it is a very high risk that it will not run as expected.
So, giving the user a dialog box explaining that this file is a Windows program, and explaining what Wine is, and explaining how to install Wine using "Add/remove programs" would be good.
But giving the user a "Install Wine now!" button would probably be a bad idea since people who don't have a clue what they are doing will then click that, and be angry when the Windows game they tried to start freezes during startup.
When people actively choose to install extra software using "Add/remove programs" they know they are doing it. Wine should not be *installed* by people who don't understand what they do. Installing MP3 support is by contrast something *everyone* must be entitled to do (provided you do not live in USA where playing MP3 is apparently illegal, unless you buy permission).