An observation from SPC14... An overwhelming majority of the sessions offered at the conference were Office 365-centric. I counted only one on-premises development session. This is a clear indication of how Microsoft wants you to be thinking.
Will organizations embrace the path to cloud-based collaboration or be dragged kicking and screaming? How much more does the cloud ecosystem need to adapt and augment their services to mitigate the objections that continue to fuel on-premises installations of SharePoint? Office 365/SharePoint Online/BPOS have been around for many years now as an option, and continually become more of a viable one. We hear loud and clear from Microsoft that their innovations will be made available more rapidly and frequently through their cloud channels rather than in on-premises updates and service packs. It is only a matter of time before those new features become cloud-only.
We're right in the middle of SharePoint 2013's reign, yet so many organizations are still on SharePoint 2010. If SharePoint 2015 is truly Microsoft's final on-premises release, how many organizations that typically lag behind the adoption curve will even end up going through the effort to upgrade when they probably should seriously consider a migration to the cloud instead?
At this point, I think it can be reasonably argued that all roads lead to Office 365. We've got phased approach options that can help us get there like Amazon/Azure/FPweb/Rackspace. We've got OneDrive for Business. We've got a commitment for one last release for the server hugging data center stalwarts. It's our choice how and when, but we need a plan and now is the time to chart our routes. The question for all of us: is the road you're driving on going to run off a cliff or do you know which on-ramp to take before you run out of runway?