I'm with Mike's customers and Brian on this one. It seems that with every new version of Exchange there's a huge infrastructure overhaul required of the product itself and not just the typical 3rd party product overhaul (fax, backup, anti-whatever, archiving, non-Exchange UM, etc.) that comes with every new Exchange version.
We were able to upgrade from 5.0 to 5.5 and from 2000 to 2003 with relative ease, but had to migrate from 5.5 to 200/2003, from 2003 to 2007, and now again it seems from 2007 to 2010. The 5.5 to 2000/2003 migration made sense as we moved from the Exchange Directory to Active Directory, but now this is starting to get silly with migrations required at every major release.
Many of the features introduced by the new versions are welcome, but migrations take a large amount of time and expense and it's getting harder and harder to justify the expense every 3-5 years, even for the desirable features.
For example, I especially like the ability of E14 mailbox servers configured with DAGs to be able to host both the CAS and HT roles. This makes high availability much easier than E12 where no other roles can exist with CCR mailbox servers. While those of us (including myself) on the technical side of things might sigh at the thought of a migration but resolve ourselves to do it for the technical gains, the people with the checkbooks say: "Didn't we just upgrade e-mail back in 2008 after 6-9 months of testing and planning the new system and at a cost of (some_big_number) that we're still paying off?" Then you have to try and explain why we should start planning another test and migration project at a cost of (some_other_big_number) for features that only geeks love (except for OWA 2010 - everyone loves that :) ). This blow can be mitigated a bit if there's a feature that's desired from the business side of things (such as archiving or discovery), but to many of the purseholders, "E-mail is working and I'm not paying for another 'upgrade' so soon."
My initial impression was that 2007 to 2010 would be similar enoug to allow an upgrade, rather than a migration. So it's suprising to even hear things like, "a separate AD site was the original plan." Really? I can't believe that was considered long enough to even become a "plan."
I know I sound really negative, but I think going forward this needs to be a little easier. The organizations I support like to stay current, but the Exchange overhauls have to stop.