I'm joining in to say that I would have him publish some books in order to start accruing royalties. That will supplement his income depending on how prolific he is as a writer. Most of my writers have chosen the author track. I've let Maaike Haas become a journalist but as mentioned above, she does have to go out and interview people. Honestly, I only do that when I get around to it so that slows the promotions a bit.
I think journalism is fine if you want something different or if you have a sim living near a lot of people who walk by. The author track is easier though, especially if you want to primarily focus on the sims in your household.
Have him get engaged, write three books in the author track and then get married wherever he is in his career by then. That's probably what I would do.
