This tour was our first experience in Italy back in 2006, and we loved all of the locations so much that we have been to almost all of them on subsequent independent trips. Also, to put your mind at ease, I did a solo 3-week trip to Italy when I retired two years ago, using many of the things your RS experience will help you learn, too. No need to be nervous at all.
“Any other essentials besides what is in the RS guide that you suggest I buy before I leave?” I do like to bring a few protein bars or similar - just because the first few days, I may be hungry from the time zone changes when it’s inconvenient to buy something.
“Pictures - Do you use your cell phone for taking pictures?” I have wonderful photo books created on-line which are one of my favorite souvenirs. I just use my iPhone. Learn all of the capabilities of your phone for great photos.
“Local plays, concerts or any other forms of night life for the older set.” Your RS guide will share options while you’re there. Sometimes 4-5 people from the tour will go together. And be sure to participate in the gondola option at Venice!
“Do I need to buy a small amount of Euros before my trip?” We always buy some Euros from our bank in the US. I don’t like making any ATM transaction decisions when I’m jet lagged. Be sure to notify your ATM & credit card company that you will be traveling out of country, so nothing is blocked.
“Hotels - Do they clean rooms? If they do - do you allow your room to be cleaned? Can you leave your clothes in the room, of course not your valuables.” Do exactly the same as you would in a US hotel. Some of the hotels might have a large wood piece or similar connected to your room key. If so, you leave the key at the front desk when you leave the hotel. And some might have the key cards that look like credit cards. Sometimes those need to be placed into a slot on the wall of your room as you enter to engage the power/lights in your room. I should mention, I do like to bring a small flashlight with me for emergencies and also to sometimes find that slot....or see where I’m walking at night.
“Night - Does it get cool?” The daytime is usually very nice, I bring a warm scarf or cardigan for the evenings while we’re eating outdoors. In the Dolomites, it will be cooler. I brought a lightweight sweater, or you could have a lightweight jacket.
I would highly recommend going to Italy two days before your tour begins. Then you will be finished with the jet lag before your tour begins. If your flights were delayed, etc. you still have time to meet the group the first day. For this tour, we flew to Milan and took the train to Verona for our first three days and then took the train to Varenna on Lake Como to begin the tour. Others can suggest other options.
I would happily take that same tour again. Have a fantastic time!