He's a loser. 27 years old and still an intern that relies on his families allowance to live.
We see in the game that he's supposed to have this potential to be a writer, but what kind of writer is he going to be? He has no real life experience, nothing that he's lived himself that he can base his writing on. I've read writers like this, and it's just junk. Based upon what they can derive from other writers or Wikipedia articles.
Ian is presented to us as the male protagonist, the other side of the coin to the female protagonist Lena. And yet Ian isn't even a patch on Lena, she's out of his league.
I would strongly disagree with your assessment.
I don't think I've known 27 year old who were extremely successful at that particular age. In Europe, it is not uncommon for people to live with their parents up to that age, especially if they're living in a big city where they can attend university of their choice.
Ian is trying to make it in an industry that's very unlike most other industries. So, working some relatively menial job while he does that makes sense to me. He covers his living expenses on his own, whether you his father for more money is his choice.
Lena is in a very similar situation - she's trying to make it as an artist and is also working menial jobs.
My criticism of Ian is that his story line sort of "promotes" him becoming a much more assertive and confident man. He starts as your run-of-the-mill, down to earth 27 year old, but most paths take him on a more dominant route. I would like options for less dominant routes as well.