It seems I made some blunder with the jessie2armhf image. It's basically unusable. The whole user configuration must be messed up. Seems like nobody else has actually tried it before.
I'll have to look into it further and will probably release a new image after the weekend.

In the meantime, the jessie1armhf image should work fine from a technical POV. It's just more outdated than jessie2armhf.

Thanks for the feedback!