I've been able to upgrade castles with my castellan after many years but as far as I can tell the castellan can only upgrade castles. So my question is how does one trigger a city upgrade after spending the cash to improve the city?
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I'll be more specific. I don't own the city it's a vassal of my county. The castellan doesn't work if you don't own the city; I've tested it by triggering the upgrade event in the console.
Just tested this and it seems to work for me. In which province were you trying to improve your vassal's city?
I've upgraded plenty of citys this way. Make sure, if your using the console to trigger the event, that it triggers for your castellan not for you. I had this problem while experimenting with my own mods