Thanks for your submission, Chris.
This week we made some improvements to the update process so that, for future releases, you will no longer have to leave Visual Studio to upgrade the ReadyRoll extension. Upgrading will still necessitate a restart of the IDE, however, as this is unfortunately a limitation of the way that the plugin system works in Visual Studio.
Having said that, we're also quite fond of the simplicity of Chocolatey installations, so I'll keep this open for the community to lend their support to this idea.
Thanks Chris! Hopefully the improvements will extend to all project types, not just csproj files, but we'll keep monitoring this to see how it develops.
ReadyRoll supports a code-first workflow through an integration with Entity Framework Code First migrations, which would allow you to use the Fluent API to initiate database changes.
You can read more about this approach in the following tutorial: