I think it would be possible to integrate migrating jailed users to/from this type of setup. My general idea is though.. Shell users like this belong in the /home directory, whereas jailed users belong much closer to the website.
I'll experiment with this more before I actually push it upstream. I think its important for admins themselves to be able to change this setting if need be, so I wouldn't push a finished versions that can't properly go both ways by an Administrator.