In chapter 11 right now, and so far she's had three "different" outfits. And by different I of course mean "the same but colored differently."
And she thinks she looks like a serving girl, or a real sailor, or whatever. Is that supposed to be some kind of a joke?

I'll have to agree with you. So far I've seen her in her underwear, normal clothes, and clothes from the innkeeper. They all look the same. What's more, they're all neutral/almost flesh colored, so sometimes she seems like she's naked. If the developers were so insistent upon using the same skin, they could have at least thrown her in some bright cyan or deep purple. She's an artist, dagnabbit, where's the color or style?

She's a pretty crappy artist if you ask me. Not only can she not complete a single painting over the course of several weeks, possibly even months, but she also thinks the little hologram of a wire-frame dragon thingy her friend made is a work of genius.

While the work of genius bit is indeed a stretch, I can understand not having a painting finished about weeks or even months. Sometimes you just get hung up. It's like writers block ... but with paint. The only difference is that careless painting could ruin a piece where as careless writing can just be deleted/re-written :p