Whether you like Caligus or not, and whether you like Dobby or not, you have to give credit where credit is due. Dobby/Caligus has been one of the few who are not scared of taking a chance and declaring a war. Almost all the big wars of late have been started/provoked by Caligus.
Yes, Dobby is like Jenred was, they actually work to keep the island interesting, even if it is a risk for their realm.