Yes, it's foolish to attack him with Wing in the castle; he'll simply crush you in open ground. Try to ambush him somehow.

Wing doesn't need defense; the first hit at level 25 will kill him outright. It's better to focus on leadership and speed aura.

You need to try to secure territory strictly to the north, where the archer dwellings and dancers are located near the castle; this is a huge bonus.

If you're using light magic, why Rain?

Two rings for initiative and a staff don't give a +50 advantage; these initiative bonuses are NOT cumulative.

Elder Druids are better; their spellcasting will be as good as Necromancers'.