I think the biggest issue may be the fundamental fact that Mailpile is software that has to run on a computer somewhere - people are getting so accustomed to just getting service for free on the web, that many will balk at having to install an app locally. Folks who value their privacy enough will, but not everyone does.
This will be a problem even assuming we solve the two hard problems and major benefits provided by cloudy solutions: backups and "always on, always available" remote access.
Getting the Windows and Mac packages shipped by Beta was a priority so we could get feedback on how they behave and have time to track down issues before the 1.0. The app is already very stable on Linux, there we just need to coordinate with the community to get packages built (and efforts in that direction are already well underway).
The DIME story is largely "wait and see", but we've reached out to Ladar and the stuff he talked about at DEFCON sounded very promising. We'd love to be one of the first apps to support it.