Itinerary..add a stop? too many days anywhere?

What is your intention with "day trips" from Bern. That is a lot of time there and not enough in your other locations. You didn't really say what it is you enjoy doing, but the more you can push back your time in Wengen, the more things are going to open up. For example, Mannlichen opens on May 25, but that does not guarantee that the amazing kid friendly walk from Mannlichen to Kleine Scheidegg will be open, as it depends on snow melt. There are also some great things in the BO that don't open until June 8 (I.e. Allmendhubel, Scyhnigge Platte, etc.) + doing Annecy would have been ideal to fly into Geneva and out of Zurich or vice versa to avoid some backtracking, but I'm assuming you've already booked your flights and that your dates are set. If not, I'd make some adjustments. If flights are set, maybe something like this as an alternative idea....

May 26 - Zurich > Luzern
May 27 - Luzern
May 28 - Luzern
May 29 - Luzern > Montreux
May 30 - Montreux
May 31 - Montreux (can do an optional day trip to Grueyere from here if you want)
June 1 - Montreux > Annecy
June 2 - Annecy
June 3 - Annecy
June 4 - Annecy > Wengen
June 5 - Wengen
June 6 - Wengen
June 7 - Wengen
June 8 - Wengen
June 9- Depart Wengen by around 7 am to make 12:40 flight out of Zurich

or

May 26 - Zurich > Montreux
May 27 - Montreux
May 28 - Montreux
May 29 - Montreux > Annecy
May 30 - Annecy
May 31 - Annecy

June 1 - Annecy > Wengen
June 2 - Wengen
June 3 - Wengen
June 4 - Wengen
June 5 - Wengen
June 6 - Wengen > Luzern
June 7 - Luzern
June 8 - Luzern
June 9 - Depart Luzern by around 8:30 am to make 12:40 flight out of Zurich

This is a trip celebrating my daughters high school graduation. She chose Switzerland being a outdoor lover and all things nature. We know that we will get some hiking in just seeing all the amazing sights. I mainly watched a ton of youtube stuff and came up with a general idea of what not to miss and try to see. I adjusted some things after asking another user that has been helpful.
5/26 arrive, go to Luzern
27 Luzern. Rigi
28 Luzern
29 head to Wengen
30 Wengen
31 Wengen
1/6 Wengen
2 head to Montreux via Golden Pass
3 Montreux
4 Montreux
5 head to Annecy via Geneva
6 Annecy
7 head to Bern
8 Bern
9 fly out

If your return flight is at 12.40 and Bern is 1 1/3 hours from Zurich airport at most, so if you leave Bern by 8:00 or even 8:30, you should have plenty of time to make the flight. There are direct trains at 8:02 and 8:31.

Be aware that there still may be some snow in the Berner Oberland. If you plan on doing many hikes be aware that some of them probably won't be open yet.

Good to know. Also, helps with packing. Which I am worried about lol

I’ll still stand by what I said in my suggestions, but if you prefer the recommendations from someone you were given, I’d recommend doing it in reverse to give as many days as possible for the snow to continue to melt in Wengen. The best hikes are there and if you have any chance of doing them you really want to be into June for that. I also disagree with making an overnight stay in Bern. That’s a doable trip from Luzern and the more you move hotel, the less time you’re spending doing fun activities. The Golden Pass is also not worth routing your trip for. It’s fine if it works, but it’s nothing mind blowing. You’ll see plenty of views without making that a priority.

5/26 - Arrive in the morning > Montreux
5/27 - Montreux
5/28 - Montreux
5/29 - Montreux > Annecy
5/30 - Annecy
5/31 - Annecy > Wengen
6/1 - Wengen
6/2 - Wengen
6/3 - Wengen
6/4 - Wengen
6/5 - Wengen > Luzern
6/6 - Luzern (optional day trip to Bern during this time)
6/7 - Luzern
6/8 - Luzern
6/9 - Luzern > Airport