Hi AJ!
If you live in Milan you'la have a lot of opportunities.
In Lombardia Valtellina, in switzerland Engadina, Ticino/Uri/Simplon also Piemonte and Val d'aosta are in a 2 hour range by car.
To investigate snow conditions and tour reports the best site is camptocamp
http://www.camptocamp.org (here you can find my profile
http://www.camptocamp.org/users/244187/it , i live north of Milan so you can find many interesting routes for you too)
Another website to find reports but less organised for Italy especially Lombardia
http://www.on-ice.it/onice/onice_reports.php?type=0 or
http://mob.gipfelbuch.ch/gipfelbuch/verhaeltnisse (switzerland)
Also
www.gulliver.it for Western Italy (Piemonte, Val d'aosta)
Avalanche reports:
www.slf.ch the best website of all..it covers only switzerland.
For Italy you have a report for every region through ARPA website
http://www2.arpalombardia.it/siti/arpal ... oNeve.aspx (a site for every region, this one is for Lombardia).
Italian Alpin Club known as CAI is very active with skimountaneering courses and in Milan they do snowboard classes as well (scuola righini for example). It's a good way to learn how to move in the mountains and meet people.
If you need more feel free to ask
Roberto