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Nicholas, sorry for the confusion here - OmniFocus does keep more than one .client file around.

At a minimum, it keeps one client file that's more than an hour old for each machine; we do this so the database doesn't compact before some other device gets a chance to add un-synced changes to the server.

If you sync a device more frequently than that, you could easily have multiple client files on the server, though.

Auto-Sync means that OmniFocus will sync when it notices the following:
  1. Changes need to be synced and you haven't changed anything in the app in the last minute.
  2. It's been more than an hour since the last sync. (This usually happens when the app starts up.)

When you auto-sync, it's important to put the phone's screen to sleep (a short press of the power button at the top) rather than putting the whole phone to sleep. Not sure that's causing the problem you mentioned, but it's one possibility.

If you let us know the specific error message you got, we may be able to help figure out what's causing it.