I wonder how he managed to reconquer his castle. By, uh... besieging it, maybe? Probably? Now repeat that eight times - and honestly, I’m struggling to see where and how exactly he tried to save his subjects.
Sorry, but losing your castle nine times isn’t what capable military leaders do.
Well if he had the loyalty of the surrounding subjects presumably there's a lot less looting during his sieges.
That's not how it worked. Armies had the tendency to eat more than the locals could provide. A region that could feed itself suddenly has to provide for thousands of soldiers. This is why war inevitably led to starvation.