Pass and Ticket Questions for trip in August

So my question is, with the itinerary listed, knowing that we don't plan on going to the Jungfraujoch, and while considering the additional remaining cost of any lift rights in the Lauterbrunnen area outside what the Half Fare card would cover, what would the benefit of getting the BO regional pass if any, and would that benefit be worth an additional $318?

Based on your set itinerary you don't need BO regional pass.
And weather permitting I think you at least want to spend roundtrip around $90 with the Half Fare card to go up to Kleine Scheideg and do this walk
https://www.maennlichen.ch/en/summer/experiences/panorama-trail.html

Sometimes one can be too tight with money and miss out on a great lifetime experience.
And the Jungfraujoch is the most overhyped attraction in the BO, and not worth it.

Thanks Jazz!

We were actually married up in KS, so we'll be going there. We went to the Jungfrau last trip.

We'll be staying in Wegen and mostly just doing some casual hiking, traveling to Grindalwald, Gimmelwald, and Murren.

So you did not include the cost of these in your calculations. From Wengen (note spelling) you can go "over the top" via Kleinescheidegg, or the valley route via Lauterbrunnen and Zweiluetschinen. so add the cost of these trips into your calculations.
Also, your calculations are based on Lauterbrunnen, but you say you are staying in Wengen. Add the costs between Wengen and Lauterbrunnen.

Also, You don't need the regional Pass for Zermatt, just 4 days in Wengen. You can buy now Saver Day passes for August 21 at 49 CHF pp with Half Fare Cards, so that is 98 CHF ( $110) That will get you back to Zurich, plus anywhere else in Zurich (or anywhere in Switzerland) for that day.

Thank Sam!

Yeah, I assume we'll have some additional costs outside of what I was able to estimate here, and I do hope to take advantage of the saver fares as well. I'm coming to conclusion that even with those additional costs, I'd be better off not getting the BO regional pass.

The BO pass has no use to you in Zermatt since Zermatt isn't in the Berner Oberland, so the 8 day pass probably doesn't make sense. Have you priced out doing the HFC + 4 day BO pass? That would give you the enjoyment/flexibility of the pass for your time in Wengen and then you'd just use your HFC for your Zermatt/Zurich portion. That's 196 chf per person with the HFC -- so it meets your options in the middle :)