Re: All is Strange in MS Land
If you are looking at running old applications then we found the best way is in a Virtualbox Win2k VM. It doesn't have to load (if you save in state) is lean on RAM and the old apps run faster than they ever did. Compatibility on business applications is excellent. Stuff that cheated to address real hardware (games?) may be a different story.
Its all free and no activation issues to circumnavigate. It even networks nicely with your Linux filesystems.
More modern stuff that won't run under even real Win2k we have used Wine. The reason is they may be pushing even the Win API envelope and hence there is a good reason why some will crash under Wine which won't handle all the ambiguities that exist in native Windows. That's what we found. An application like Evernote would work but later updates would not. Wine 2.0 may fix some of those issues but we treat an application with Wine as an opportunistic and potentially unstable platform. Not really for mission critical work.
I see Wine as a transition aid to smooth the migration to Linux. To give people time to acclimatise to Linux and adopt Linux/Cross OS solutions as replacements over time.
Worked for us and thanks to the Wine team though we no longer need it. That's success.