@BurningCold @MokleyTotally understandable and I had some of your same concerns as I was writing. I'll try to address what you're saying point by point. As I said if people feel Rowan is being played unfairly I'm happy to make changes.
I don't see how he's wealthy if he's fled his kingdom and by extension any riches it may possess.
I don't think it's totally unreasonable to assume he made out with money. If one was leaving there home for what would likely be a large amount of time they'd probably bring some money- especially if they knew they were going to be living somewhere else for an indiscriminate period. I'd imagine as he was making preparation to leave he loaded a couple of chests of gold onto a carriage.
Additionally, he's technically not a prince if he's neglecting his duty as a prince by LEAVING the kingdom.
Well, this is more of a semantical issue. Sure, he might not technically qualify as a prince, he's more a royal exile, but I don't really see how this is a major issue. As far as most people would know he was forced out in a coup, so it's not like he exactly up and left randomly- in many people's eyes he would still be a prince even though he's not officially filling the role.
Also, if the land he hails from is so far away that people are only going to hear bogus stories and not the clear truth, it's unlikely people would even know enough about him to care that he arrived/believe he's really royalty in the first place.
He's not Kim Jong-Il scoring 11 hole in ones the first time he picked up a golf club. I may have put a little bit too much emphasis on the aspect of tall tales- something more like 'hey you here in this one place this one guy was born and they think he's going to rule the world? lmao'. As for credence to his identity it wouldn't be hard to establish- there were a lot of ways for royalty to identify themselves way back when. A ring with a royal crest, a letter with a sigil, etc. Maybe I also stressed the concept of 'distant' too much- I could spend some time fleshing out Rowan's kingdom, make it closer to Winding, give it an actual name, etc. Also, the clear truth isn't entirely clear to his people either- after all, it's not as if most peasants get a front row seat at the ruling populace's liveses. What they've heard surrounding there prince's disappearance and the wars that have begun in his absence are little more then rumor, rumors which he did his best to make sure spread in his favor. He had considerable power as a prince and access to many key figures in the ruling class- it wouldn't be hard to craft a false history by spreading his story to the right people.
People don't have simple minds here in Winding and this isn't a D&D game so he can't just be super good at manipulation because he wants to be.
I say to this: Why not? I don't see how it's inherently bad to have a manipulative character- of course 'manipulation' as a skill can sometimes be used in pretty OP ways, but in this case I feel like what I've written is played fairly straight. If someone showed up with a lot of money and is spending it to help people out around your town you'd probably be pretty biased to like them. A VIP shows up, gains a positive reputation, and after a while people will probably be willing to vouch for him. Of course he's not just good at manipulation 'because he wants to be'. He's been groomed to rule a country- of COURSE he is able to lie and cheat. Added to the fact that he's basically a psychopath he make a pretty good liar. It's not as if rulers being able to manipulate doesn't have a basis in the real world.
Those are my thought. Of course this whole idea of Rowan being in a position of power came kind of last minute, so there are probably some holes in my logic- feel free to pick at them. Take all this with a grain of salt as well. This isn't totally Rowan's official history, more just me ideating how it might be and seeing if that falls more in line with something that makes everyone happy.