Last update included a database upgrade and it was pretty simple done from the nuget console, the tricky/not so fluent part was when deploy to test or live system.
It would be great if you could implement that doing this automaticly in a InitializableModule or something simular so even deployment to other enviroment than development can be as fluent with this as it is with ContentTypes.
A billion times YES.
Inform us (readme.txt in the nuget springs to mind) in a way we cannot miss, and do the upgrade on application startup. That way we can know if we need to be careful when deploying, doing it late at night or the like...
As you probably know already this is supported in both CMS and Commerce since a while back. More info: http://world.episerver.com/documentation/Items/Developers-Guide/EPiServer-CMS/8/Deployment/automatic-schema-updates/