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If you own the city, and the holding, can't you simply send your Castellan to improve city on Bear Island?

No it seems I cannot. All the castellan does is aid in the construction of the main castle after you have paid for the single upgrade. However, there is no such way to purchase said upgrade for the city holding. Maybe this is now irrelivent however as when I start the game now it crashes after I play for a few days....Ugh...Any Suggestions... Also, Even though I am "Lord of the North Clans" it keeps giving me as the title before my name Lady, even though im a male. It is only like this for North Clans... So pissed....I was Lord of Bear Island, High Lord of North Clans, Wolfswood, and Skagos....