Salut Craig,
Paradoxically, I will be outback in BC and will be returning around end of March. Maybe when our dates firm up, we can meet up.
Otherwise, in 20 years you will see that the city has cleaned up a bit (thank God, it couldn't really get grimier!).
I'll start with the easy side - camera shopping. You can find alot here, but the prices will send you away screaming bloody murder. Oublie.
Easier still - good food:
Trattoria alle Colline Pistoiesi, Via Amedei 1 (next to Piazza Sant' Alessandro)
Great trattoria, tipical simple dishes, my second kitchen. Booking recommended.
L'Ulmet: Via Disciplini
Take italian food and apply the french savoir-faire for taste, presentation. Add an incredible wine collection (visit the cave if you can). A bit pricy and elegant, very good food.
Consolare: don't remember the street, in the heart of Brera.
Where excellent fish and seafood meets the fashion crowd.
Arrow: again, have to look up the address... zona Corso Sempione
Where even better fish, less the fashion crowd
You have to do the "aperitivi"... from 7 to 10 the past time is to meet at the bar and have a cocktail or three while grabbing the incredibly opulent servings of munchies each bar puts out. Great for people watching... some are:
Living - Arco della Pace (angolo via Bertani) closed Mondays
L'Exploit - Colonne di San Lorenzo
Le Biciclette - Via Torti (zona Porta Genova)
And for the hardest part - sites to see.
Presumably you have seen the majors like Duomo, Galleria, Scala, Cenacolo...
Brera houses the current Università delle Belle Arti, and is quite an interesting visit.
Corso Como, from Porta Garibaldi to Porta Nuova, which 20 years ago was a craphole designed for mugging and drug dealing, has transformed into a design/hip/art pedestrian area with the requisite cafés and boutique art galleries. Amazing transformation.
Other than that... it's Milan! People watch! ;-)
Anyways, if more comes to mind I'll chime in.