The time zone setting for the task is used to determine when Proby should be expecting a notification from that task. We're still thinking of the best way to display the times on the dashboard. Listing all of the tasks in the same time zone makes them easily sortable based on the last execution time (we could still support this sort order while displaying the tasks in their configured time zone...but it may be more confusing if each time was in a different time zone). We've also thought about listing all of the tasks in the user's time zone. Jury's still out on this.
Representing the cron schedule in some other format is also feedback we have received before. I just haven't found a way to cleanly and concisely display the schedule in a format other than the cron format.
Regarding the downtime...we don't manage that right now. We're running on a single VPS. The goal of the beta is to determine if there is enough interest (and potential financial support) to deploy Proby to a more robust and fault tolerant setup.
Thanks for the feedback!