We've been to Milano, Ravenna, and now in Padova.
1) We have had problems with getting on the internet. I brought my mobile hot-spot device, and this is what I am on now
2) Keep your passport handy (not in your moneybelt) on the train. They may want to see it.
3) Trains run on time. You get about 2 min to get on. Don't be late to the station.
4) I have seen no sign of pickpockets. Now, the observant reader will note that a pickpocket that you can notice is a very unskilled pickpocket. At Milano Duomo square, there were a lot of cops. At Milano airport, nothing obvious. The most blatant case was some woman in Ravenna asking for money in the railway station.
5) APERTIVO TIME!!!!! This is such a fun thing. In Italy, between 6-7 PM, many bars do Apertivo. It's a cocktail hour, of course. The main thing is the Aperol spritz - Aperol is a cordial with an orange flavor - the spritz is a fizzy water. Also Campari spritz. These are often served with a little snacky snack, usually potato chips and sometimes olives, but some places do a little pizza.
6) In mid-September, NOTHING is crowded. We did not try to walk up to the "Last Supper" and get in. But here in Padua, we could have walked up and gotten immediately into the Scrovegni Cappella. Railway stations and some piazzas have been crowded. But not many lines here during Shoulder Season.