Lurker, I get that it can be intimidating, but if you have time you could practice planning an itinerary and see that it isn't as difficult as it seems.

There are basically 3 types of trains REGIONAL are slower with many stops, INTERCITY with some stops and I think the high speed direct trains are called FRESCCIA?

We used the OMIO app to research schedules and purchase tickets on our cell, tt worked well. They have a website you can look at without purchasing the app to experiment. There's also the Italiarail and Trenitalia websites to practice looking at schedules and pricing. Prices are about the same online and in person.

Purchasing online was convenient when we knew which train was best to get where we wanted to be, such as this Milan to Santa Margherita trip. It also allowed us to choose seat assignments for this longer leg, my wife prefers to face forward!

Buying tickets at the stations can be done easily with the ticket kios system, user friendly and they offer English. Or just go to the counter, English may not be spoken but at least knowing the name of your destination will be enough to get a ticket.

Now knowing where you're going sounds simple, but larger towns/cities may have multiple stations spread out around the city. With google maps we would find the station that was the most convenient to our airbnb's, example this trip from Malpensa Airport the kios showed departure from Malpensa T1 or T2, confused we asked an attendant for help and realized we were in "Terminal 1". Milan has many stations, we googled and found Milano-Cadorna was closest to our airbnb so we chose that regional train. We could have gone on a faster Intercity train to Milano Centrale but it was a longer walk.

When we do day trips we still check schedules and then arrived a little early to use the kios, takes cash or credit. Short regional trips don't require seat assignments, but longer Freccia's did. The ticket shows your car number, We always arrive early and watch the big train schedule board like at an airport. Once they post the track or Bin number that means the train is there and ready for you to board. With luggage it's good to be early to ensure a convenient rack to put it in. Sit down and relax, a conductor will soon stop by to scan your ticket either paper or on your phone. Eazy Peazy!