Best pass for travel from Milan to Lauterbrunnen and then over to Zurich

I don't know how to figure it other than just writing down the amounts for different options, which you can do with the SBB website. Note it gives prices assuming you have at least the half fare pass.
This is a very fast paced plan to be doing with teens in tow--have you crowdsourced the itinerary? That is the help I would focus on for now.

That’s a lot of ground to cover in 10 nights. In order to determine what pass is best for you, you’ll need to have a list of activities you’re trying to accomplish in your time and then price them out on SBB.ch (prices default to half fare card pricing).

You’re not asking for my advise on your itinerary, but I’ll give it anyway :) You have some major travel days involved to get between all your stops. For example, staying in Rome for 2 nights and then having to get to Sorrento, you really only end up with 1 day in Rome. Then you’re going “backwards” down to Sorrento and then spending another day getting all the way to Milan. I’d highly recommend removing 1 of your stops to actually have time to accomplish anything other than spending time on trains.

We actually arrive in Rome at 8:00 am, so we have two full days in Rome which is all we really want. We are considering the golf cart tour to cover a lot of ground in a few hours and a Colosseum visit. Then we have 2.5 days in Sorrento to do an Amalfi coast boat tour and a couple of hours in Pompei. Morning train (5 hours) to Milan to arrive at check in time and we reallyhave no desire to do much in Milan other than walk around the Duomo and maybe spend the full day doing a day trip to Como (maybe not). Lauterbrunnen will give us 2.5 days of exploring and I wish we had more. Late afternoon train to Zurich to Hyatt at airport to spend the night and travel out the next day at noon. It's a lot, but we aren't the type to sit around and relax as we can do that at home. My main quesiton is the portion from Milan to Lauterbrunnen with several of the sites to in 2.5 days and finishing up in Zurich. It seems either the Swiss travel pass, half off pass or a regional pass would be ideal.

3 day or 4 day Berner Oberland pass may be your best option. It covers all cable cars and gondola rides from Lauterbrunnen and Grindelwald (with the exception of Jungfraujoch and Schilthorn which you can ride at a discount), boat rides in lake Brienz and Lake Thun, travel from Domodossola (Italy/swiss border) to Lauterbrunnen and travel to Bern on your way to Zurich. You need to just buy train tickets from Milan to Domodossola while entering Switzerland and ticket from Bern to Zurich on your way out, if you buy Berner Oberland Pass.

travel from Domodossola (Italy/swiss border) to Lauterbrunnen

must be done on the one hour slower - but scenic - train f you want to use that BO pass. The high(er) speed trains from Visp to Spiez are not covered,

And if you are going from Lauterbrunnen to Zurich the day before your flight, go via Luzern for the very scenic train ride to Luzern. Takes a bit longer than going through Bern, but worth it IMHO. The ticket is just a little cheaper as well.

This is all very helpful! Going to take some work to figure it all out but thank you for the guidance so far!