We put together a ChipworkX updater application. It will erase the device then update TinyBooter and Firmware from the SDK.
So when the firmware needs to be updated, just run this application. No need for a command prompt or MFDeploy.
Hopefully, this will make things easier.
UPDATE
The ChipworkXUpdater.exe is now part of the GHI NETMF and .NET Gadgeteer package. Which is #3 under system preparation.
I believe you can select any files to download. Put the firmware and the application files in the same folder and select them all together. It should work. Let us know if you have problems.