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You should look in the events folder for 'job_castellan'. I know that at least the first event in that file works for manually triggering the upgrades while your castellan is using the 'improve holding' in the county you are upgrading holdings. Note that you must use your castellan character id while triggering that specific event to work.
For example:
Code:
event 950 CASTELLAN-[B]CHARID[/B]
Edit: Other ones might work too, but I've not tested it or looked at the codes for those to confirm that.