Yeah, I'm a proponent of Storm Front being set in 2000- makes chronology a ton easier.
Also, one thing I picked up re-reading Death Masks- it's an election year. (DM 116). Does that help any?
EDIT: City elections are every four years- 2003 being the most likely (too late in the series to be 1999 or early for 2007)- making 2000 Storm Front.
I HAVE SOLVED THE TIMELINE CONUNDRUM. Nobel Prize, please.
In terms of being easier to calculate chronologies, yes, setting Storm Front as if it were 2000 would be way more convenient. In terms of when they were actually written, and unless Jim was for some reason intentionally setting the early books future-dated, IIRC Jim has said in Q&A sessions that he had written SF while still at the University of Oklahoma, and also that Fool Moon and Grave Peril were ready before Storm Front eventually sold.
Since SF was published April 2000, it would seem that those were written in the late 90's. For Harry to be about a year younger than Jim, Harry would have been 25 in 1997.
The only other real-world date that comes to mind is that Stroger replaced the old Cook County Hospital in December 2002. Of course, hospital construction must have been in progress for quite some length of time before that, so Jim could have become aware of the upcoming hospital move some years ahead of the actual move if he was tracking major Chicago planning.