I probably visited when you were living there, Sarah. It would have been a real pleasure to meet you and visit you then. (For that matter, I think it would also be a pleasure to meet you now.)
I have vivid memories of my visit to Milan, which was really the first Italian city I ever visited (I had previously made a foray into the Italian Alps). I was advised that it's not the most historically signficant or picturesque city in Italy, and some would probably say it's the least. But it stole my heart. *cough, cough* Seriously though, that visit was unforgettably exciting, in much the same way that my first visit to New York on my own was unforgettable.
Back to the topic, and sorry for the digression: my suggestion is that it's not crazy to plan an aggressive itinerary if you build in flexibility, such as the ability to make cancellations and have the information at hand to make different reservations or plans as you travel. That's a huge advantage to having the Eurail pass, after all, right? That's always how I travel, and it allows me the flexibility to make it into a fever-pitched trip in which I can see as much as possible in the allotted time, or to slow down and savor, and enjoy the experience of the places I am in during the course of the trip.
Have you been to Rome and Paris before? If not, I think those are two places you gotta go sometime, but it doesn't have to be this time. Just my humble two cents.