To be fair, some rural prince wouldn't stand a chance in hell typically. Roland's improvements to the territory, especially in such a short period of time, are completely alien. Any sane person would think the 4th prince is acting a fool.
I really like red haired guy. He's not overly pretentious or obnoxious, but rather self-aware and cognizant. Furthermore, he has enough sense to be wary of someone he is unable to completely gauge whereas other nobles like his father is completely dismissive and will not believe in small possibilities.
"Can you fight like your ancestor did when all you've known is peace" is one hell of a line from a side character. Red hair guy could make for an interesting enemy or a beneficial ally.