Upcoming trip to Rome - How did I do?

Not sure why you are going to Pisa. I would suggest spending two to three days in Florence instead of going to Pisa if you are headed that direction. One night in Florence is not nearly enough.

Are you flying out of the US/Canada/? on December 28 and arriving in Rome on December 29? You may be different, but I'm too jet-lagged and sleep-deprived on my arrival day to make any use of a museum pass. My arrival days is for wandering around outdoors and getting oriented, not going to sights that charge entry fees.

I've never tried to visit Naples and Pompeii on a day-trip from Rome. Not sure how rushed that will be.

Read a lot of queries about doing a day trip to Pompeii from Rome. It is 'possible' but have not seen anyone who has done report that they "enjoyed" it. What I have seen is that it was a very long tiring day, for a good cause.

Suggest spend more nights in Florence, do day trip to see Pisa, and have an overall better/enjoyable trip. Skip Pompeii this trip

If you choose to do all the stops you list I would NOT schedule the day trip to Pompeii the morning after your return from Florence. Nor would I plan on the Vatican museums the day after returning from Pompeii.

I am going in October. My plan is to spend 4 nights in Rome. On the last full day we are taking a bus trip for the day to Pompeii. Yes, it will be a long day but probably the only opportunity I will ever have to see Pompeii. We opted for the bus trip instead of doing it ourselves to alleviate stress.

I'd suggest either cutting Pompeii or cutting a day from the Rome part and staying an extra night in Florence.

Florence to Pisa and back to Florence might make more sense than Florence to Pisa and then onto Rome.

Given me a lot to think about.

We have been to both Rome and Florence on a previous visit.

We are only going to Florence for a day because we have specific things to see, not trying to do too much (Uffizi and Pitti Palace)
We are going to Pisa just for the tower and dinner.
We are taking the train for both day trips (Florence and Pompeii)

We are not planning more than 3 hours in Pompeii, I have read other places that longer is just repetitive and exhausting.

We are not planning more than 3 hours in Pompeii, I have read other
places that longer is just repetitive and exhausting.

I would kindly disagree with that (I've been twice) but I guess it all depends on how interested you are in what there is to learn about the site.

I have done a day trip to Pompeii from Rome. It's doable. Go all day. It's well worth it. If you decide you don't want to them Ostia antica is awesome and much closer.