I think that you'll have a smoother experience by upgrading to each OS once it fits your business needs. The bigger question is why are we upgrading? What problems does it solve/create? Are there alternatives? How will applications work? Do they need to be upgraded? Does the upgrade require new hardware? How much user training is required? Etc.
In your opinion piece on Gartner's recommendation that IT not skip Win 7, you said this:
'Ever since I've known Microsoft it has told IT not to skip operating systems, that skipping one level only makes moving to the next harder. Of course it doesn't hurt that Microsoft gets paid for each step along the way.'
Sorry, but that's flat-out wrong. Microsoft enterprise licenses have included downgrade rights pretty much always. A Win 8 license allows an enterprise to install Win 7 today and Win 8 next year without paying Microsoft 'for each step along the way.'
Just plain sloppy, and straight-up Microsoft-bashing. You're better than that.
Disclosure 1: I work for Microsoft.
2: I am not an authorized spokesman for the company.
3: I recall recently reading that current EAs were modified by Microsoft to include downgrade rights from Win 8 to Win 7 but I do not have a handy reference to cite.
In this case, where the two OSes are very similar, I can see no structural reason to not skip Windows 7 and go straight to 8. However, I do agree that changes in Windows 8 make testing and evaluating essential. Apart from the interface change there seem to be some AD Domain networking related quirks in Windows 8 that weren't there in 7, and I am not sure that program compatibility is exactly the same between the two either. Of course end user training must be considered given the significant change in the interface. Some wish to downplay that part but experience has taught me that changes much smaller than this one are enough to create havoc.