Ask HN: How would you turn around/re-imagine a city website?

I work a couple of days a month on a 'city site' for a fairly large city in the UK, doing maintenance, clean ups etc. It's been going since 1998 so it's pretty established in internet terms but over the past couple of years has really lost its way and I'm struggling for ideas to revive it - I fear I might be too close to have some kind of revelation.

Stats-wise, the site has settled at around 2500 uniques per day and has remained at that level for maybe the past 2 years. So it's not like no one ever visits, more that here is no reason for them to ever come back. It also has a very good domain (think CITY.com). Recently it has paid its way through crummy Yellow Pages-style adverts which are also drying up - and hurting the site in the process.

So, in short, assuming you had such a site at your disposal and had carte blanche to make changes - what would you do? How would you approach such a site?

I'm hoping to turn this around and make a success of it but right now struggle to think how. Any ideas are welcome, no matter how outlandish!

p.s. In case it wasn't clear, it's currently a city guide to hotels, restaurants, shopping etc - but hopelessly outdated and ad-filled.