You would simply setup your first blackberry with the default settings you want. Use BB manager to backup (backup/restore->backup) the current settings while it hasn't been activated on BES yet.
Now I would use app loader to reload the whichever OS you plan to use. Delete everything and don't backup or restore.
After the wipe and OS load is done, choose backup/restore->restore. Choose the file you backed up from the first device. Do this for each subsequent device.
Alternatively, if the devices are already wiped and have the OS version you want on them, just do the last step with the restore. Will save a bit of time.
For the second question, I think so. You would just have to make sure you don't get the PIN numbers confused. It will only connect to one device at a time (though you can choose the device under connection settings). I have connected and configured up to 8 devices connected to a single computer, but as I said, you will only be able to work with one at a time.
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