Thank you all for your suggestions. I really appreciate it!

Question: after watching one too many youtube videos on Jungfraujoch Top of Europe trip and thinking about the experience (and possibility of seeing nothing) versus the price tag, we are so close to calling that part of our trip off. It just seems way too overrated (we live with snow/ice in the winter fyi). Will we regret it?

We are also thinking about adding Annecy, France by removing a day from Montreux. We like the combo of France/Switzerland/Italy and most likely won't be in this area again. (we love nature/hiking/long walks and exploring in small towns).

Our revised itinerary:
Arrive in Geneva
2 nights in Montreux
3 nights in Annecy
3 nights in Lucerne
4 nights in Bernese Oberland (Lauterbrunnen,Murren, Wengen, Brienz)
2 nights Zermatt
4 nights Lake Como area (haven't decided on where to base ourselves)
Depart from Milan

Another question - my sister thinks she will get home sickness beyond 14 days. If you absolutely must remove something here what would you remove?

I would say Zermatt could go if you are going to visit Lauterbrunnen etc. and need to cut a couple of days.

IMO, three nights in Annecy is WAY too much. I'm glad a saw it, but was bored after less than 24 hours -- and I don't bore easily. So my answer to your question about what to cut if necessary would be Annecy.

FWIW, I think you may be underestimating how "French" the French parts of Switzerland, or how "Italian" it's italian parts, etc.

I skipped Jungfraujoch, so maybe I shouldn't comment, but I've never regretted having skipped it.

Thank you kja! Skipping Annecy (makes our trip easier to be honest) and Jungraujoch. I probably am underestimating a lot of things :-).

Question: after watching one too many youtube videos on Jungfraujoch Top of Europe trip and thinking about the experience (and possibility of seeing nothing) versus the price tag, we are so close to calling that part of our trip off. It just seems way too overrated (we live with snow/ice in the winter fyi). Will we regret it?

Impossible to know if you will regret missing it. I've visited it at least twice, but would never have gone had the weather been poor - I absolutely would not buy tickets until you know what the weather will be like. We bought tickets the day of, but these days I'm not sure that's possible in high season as most first time visitors to Switzerland want to include the Jungfrau.

But, if you're anything like me, just knowing that every first time visitor to Switzerland wants to visit a certain place is enough to make me not want to go there:)

There's a lot to see and do in the BO without including the Jungrau, and the Schilthorn above Murren is a good alternative IMO and IME, if you're still drawn to a mountaintop.

I thought the Schilthorn well worth a visit! :)

IMO it' doesn't make sense to go from Geneva to Montreux, then backtrack all the way to Geneva in order to see Anney, then go again back to Geneva and Lausanne and along the boring itineraqry (no Golden Pass!!) to Lucerne.
Zermatt - Varenna takes 8 1/2 hrs in summer and 5 1/2 hrs until end May.

In addition to my post above (actually hidden by a moderator):
Zermatt is in the heart of the Alps, with tons of easy accessible glaciers. Therefore, there is absolutely no need to go to overcrowded Jungfraujoch, nor to Schilthorn.

I doubt that it was "hidden by a moderator." More likely, it was caught in an automatic filter over which the moderators have no control. I do wish you would try working in the “Testing Area” to determine why so many of your posts go to moderation and -- more importantly -- figure out how to avoid that outcome.