I think Ian will finish (and optionally win the competition) it in the first part of the story. I mean, how long can you drag it out?
I've assumed that since it has a unique associated fight mechanic in the game, that at least it will be an enduring theme. You could be right that the tournament concludes early, but then I would assume a career option as a professional fighter might open up to winning Ian's (or Jeremy's).
I wouldn't mind such a path, especially if such a story were to be spiced up in variation between the establishment of various romantic relationships. It would be fun to see how different partner options would respond to an Ian adapting to that life. Lena has already expressed disapproval for violence so it could at least be a dramatic background for their relationship, and it would be fun if any of the other options, Cindy or Alison for example, were to more readily approve.
It would be interesting if you could have routes where Ian and his chosen partner could become a semi-celeb power-couple - and this could happen with both the fighting and the writing routes - for example if Cindy or Lena become professional models, or if Lena becomes a musician, or with Holly as an established writer.