She doesn't come off all that young to me (31!) - nor "not bright" - just odd. Her musical mindset appears to share a lot with Moz', even though her writing, singing and overall style are diametrically opposed to his. They're both disinterested in convention to the point where they may not see it when they try to look at it, and their intended relationship with listeners is similar - personal (for a long time, I've read, her self-released CD's were sent to fans in elaborate packages festooned with stickers and decorations) and confrontational without ceasing to be basically human.
I think there's a lot of wit in her visual style, though I find the wit of her songwriting limited - it's all about the emotion and the voice for her; the lyrics are just amplifiers. She does get off some phrases and rhymes I like, but by and large the backbone of her songs is the selection of theme. Fortunately she has a knack for that; she's exceptionally good at being impolite, as in her rant ("You Ruined Everything") to a more successful lover who "fulfils me in all ways," but whose help has harmed her on a variety of levels. The song makes Kristeen and her lover both sound almost irredeemably nasty, and yet there's enough identifiable truths in it that it comes off as a statement of faith. People have found artistic success on significantly worse than the ability to do that.
At the same time I find her use of her talents can cross the line into preciousness - the anti-Ten Commandments schtick of X is the classic example. Kristeen seems (to me) to very obviously live in her own world with her own values and her own priorities, and sometimes to take that to the point of losing touch with what might get to us - to mis-aim, and mis-aiming a voice like that is sort of like mis-aiming a howitzer. But her failures aren't my primary impression of her.
I think it's peculiar, though, that she identifies so strongly as a regional (Midwestern) and outsider artist, but still lives in New York and makes an incredible amount of her wish to get properly signed (she was signed to Attack!, I believe, but that seems to have lapsed with the death throes of Sanctuary). I also think that there's some sort of weird standard at work if, given her very reasonable level of talent, she truly hasn't found a single label -not even the smallest indie?- who'd take her...and then, initially, I found it hard to see past the fact that most of the success she's had thus far has been due to the help of the various prior-generation artists who admire her - when I'm sure it would've been possible for her to convert a reasonable fanbase through some method that didn't, by its very nature, make people think less of her. Surely it wouldn't kill her to try and drum up some support among the smarter metalheads, for example, who in my experience love synths and opera-voice and high camp and offense for its own sake. But I don't know anything about the music industry, and if I judged artists primarily on how they handled their professional lives, I'd be a much more confused and unhappy person.
Kristeen is the only artist Morrissey's introduced me to that I've really fallen for. I'm really looking forward to seeing her on the U.S. tour; I think she and Moz go down well together, largely because they oppose each other so violently. She's not an ideal, but she's original, genuine and vocally remarkable, and she deserves more chances than she's getting.