As far as Wine "catching up" to the newest stuff Microsoft releases being an ongoing game, the news is a bit better for Wine than for Libre Office. Wine only needs to implement the crazy new APIs Microsoft creates when they're actually being used by applications. At the very least this gives us considerable time leeway -- not having a Direct3D 10 implementation didn't hurt Wine much when every game kept having a Direct3D 9 fallback for a few years.
I would pay for such a packaging (separately from the key). What this gives me, is the latest compatible Microsoft Office in lockstep with a wine release. I would'nt even mind you charging a few bucks for every incremental packaging.
I daresay that this is a large enough pain point and people would'nt mind paying a few bucks. I would also argue that this would substantially improve the sell of Linux to enterprise customers who can have a decently working Excel at a click as opposed to the seriously cumbersome install on Windows.
It suffers from some graphic bugs (mostly in the properties dialog, for objects in PowerPoint for example; usually you can fix it by reloading the dialog), also, TrueType doesn't look perfect. I can't remember having it crash heavily.
I needed MS Office because while Open/LibreOffice is good enough for most things, and is actually more than sufficient if you write your materials from beginning to end in them and never export to proprietary formats (i.e., always keep saving in ODF), the compatibility layer with MS Office is not perfect and is not sufficient for more advanced things (such as the fancy 3D-and-the-like styling options my colleagues insist on using). The imperfections* of the document compatibility layer become a problem when working on the same document with people who use MS Office.
Using a virtual machine would probably work, too... if I had an infinite amount of Windows licenses. I can't use the license from my real-hardware install, as I still need Windows-on-real-hardware for a few things (to do with drivers and device flashing).
Using Office was the main reason why I had to reboot into Windows, and so I couldn't be happier with this setup. My productivity has increased a lot (no need to wait for reboots). Besides Office, I also use Wine to run the emulator of a platform for which I develop software (the emulator is not open source, and are not available for any Unix but OS X, which I don't have access too). So Wine does a really great job for me, doing things that I think can be called "effective usage" (in fact, I don't run any games under Wine).
* MS Office import/export is actually quite good for a FOSS piece of software, and while the "imperfections" are being perfected as new versions are released, Microsoft too keeps releasing new Office versions with more shiny features, so I understand the difficulty on keeping up with the compatibility on closed formats.