Love to hear your stories. I'm just wrapping up 45 days in Italy alone scouting places for my wife and I to retire to soon. Lodging in twelve towns plus day-trips to other locales along both coasts. Things I learned (most by trial and error, and error, an error):
Toileting: Always know where you can find a restroom, and keep some 1,00 euros in you pocket. There are precious few "public" restrooms in Italy. The good ones cost, usually 1 euro, or 1,20 euro at Roma Termini train station now. The pay potties are generally staffed, clean and have toilet paper, soap and hand dryers. Its cute in Pescara and Remini train stations that you buy a paper ticket from a uniformed staff person to use the loo. The free toilets, usually in parks and more remote train stations, are "you get what you pay for." No public restrooms at grocery stores. If holding it is a problem, best to wear some incontinence undies. I resorted to making my own - don't ask how. Alternatives - plan to pay for a cappuccino so you can use a cafe's potty - it may be your only choice at times.
Strikes: Be cautious about relying on trains on weekends. Trains are my favorite way to get around Italy. And train unions are good about announcing strikes days in advance, planning them usually for late Saturday to late Sunday. But twice I was caught trying to find options to necessary Sunday morning travel hops. First involved a one-hour wait for a two-hour sardine can bus ride just to travel 25 miles - see toileting notes above. The second required changing lodging in the next planned stop and eating the cost of the one night 's stay so I could get outta dodge before the strike hit.
Lodging. Read the fine print on BnB booking sites. I like to have a kitchen make my own meals and a washer to - ya know - wash my clothes. One place I booked said "private kitchen" and "washing machine" in the amenities section. "Private kitchen" meant a shared eating area with other guests at 5 euros per breakfast, and "washing machine" meant access to the house washer, at 10 euros per load. Another said "whole apartment wheel chair accessible" when the bathroom - the most important area to be accessible - was anything but. Thankfully I'm ambulatory.
Pet Peeve - Recycling, or Lack Thereof: Recycling can get complicated in Italy, but its a good thing. Just about all packaging in Italy is designed to be recyclable. It seems each town does it differently and it can be a learning curve each time. But it would be nice if bnb booking sites had green star or little tree symbol for lodgings that truly recycle. I would have changed lodging at one place when I found they didn't have recycling bins. The owner/manager said just to watch for when bins (owned by neighboring properties) were put out to the street and then put my recycling in those bins. Or, he said, just use the little (mixed) waste bins along the street. It dropped my rating from a 10 for that bnb to 5 or 6.
Siesta: Or more correctly "Riposo" in Italia. If you need to buy some ibuprofen or a sock or even a piece of jewelry in small towns to mid-size cities, do so before 1:00 to 1:30 p.m. Why? Because nearly every store front shuts tight until 3:30 to as late as 6:00 p.m., so that shop keepers and staff can take riposo, Not sure if folks go home and nap (makes sense in the heat of summer; in mid-February I dunno) or just lay low in a cafe for a while. Many businesses will post pre-riposo hours and post-riposo hours, but they ain't always accurate. Downtown avenues that might have been teeming with car and foot traffic all morning can be ghostly quiet til evening. One of the exceptions are coffee bars and cafes, which do a healthy trade during riposo.