Trust and Relationships
Googles failures with Gmail are well known and they are gaining a reputation as a vendor who sells thing of questionable quality.
Worse, they tend to do some incredibly foolish things with regard to EULAs, which effectively translate ownership of things that were written or created using a Google tool to Google. They have promised but not yet delivered anything approaching a solid cloud-based application offering. And the reliability of this phone solution isnt yet known but suspected to be buggy and unreliable.
Apple isnt much better. The latest iPhone has had a series of nasty problems and Apple has generally treated IT managers as if they were clueless idiots.
They dont think of IT as partners for anything and have a nasty habit of trying to cover up serious problems like security exposures. Trust doesnt run deep with Apple outside of Apple shops and this suggests that both companies, for the moment, are tied at equally bad.
I do think Google will resource this to fix it long before Apple even considers trying to work with IT again. So my expectation is that, while theyre currently tied, Google will eventually win here as well.
Wrapping Up: Who Wins
If we went by category Google would win by a landslide, but the first category the buyers themselves in most companies easily overrides almost all of the others combined.
This suggests that favoring Apple might have the better path if it werent for one thing: the Chrome browser.
This browser, as an application front end, will exist broadly on both G1 phones and PC desktops, allowing IT to more easily roll out cloud-based applications that will run on both platforms. If Google can create compelling devices, coupled with the fact that Google is agnostic about both carrier and cell phone manufacturer, will push Google ahead. They will emerge more dominant, much as Microsoft emerged more dominant after the first Mac vs. Windows wars.
For the enterprise it is all about scale. Both Google and Microsofts models scale better which, in the end (much like it impacted the Mac) are what makes for a winning combination. In the end, for the enterprise, I think we will have Google and Microsoft battling it out for the top position and that this will be a fight for the record books.
In closing, and on a related subject, if you are planning to get a G1 you might want to wait until late November or December and until we both know what the major bugs are and know that most have been corrected before getting one of these G1 phones. Generation One products tend to be a problematic and it generally is better to let someone else experience the initial pain.