After attending the Sitecore roadmap session in Boston a few weeks back, I've been wondering if we should recommend to our clients whether they should wait until the new version comes out? There are many exciting new possibilities that the new software provides. Mainly, these include unstructured content and lots of it. Along with faster database performance, and we've suddenly got a CMS that can truly scale to the largest of sites, yet have all the modern day features that most of the CMS granddaddies don't have.
So with all these new features why not just wait until the next version? The challenge in waiting is that there's no release date yet! If it were a month to wait - maybe, but there's a bit of time before this release hits and lots of web things to do in the meantime. Getting your content organized and up-to-date within Sitecore's current structure and getting it ready for the next major Sitecore release is something each current Sitecore customer should be doing, well - now. This is especially true if you haven't been keeping upgrades current in a while. The jump from an older Sitecore version to Massive will be quite challenging. Even more so if you've been a bit willy nilly about best practices and allowed end users a bit too much freedom.
Ultimately, as with any new technology, you don't necessarily need to be the first to jump in with both feet either, so if you're implementation and version upgrade cycle finds you a few months away from the new software, you might be just fine with the the current version as well.