Great discussion where I don't necessarily see that one point is right over another as much of this is on preferences for how to view information. I'll try and add some color from my knowledge of the travel industry and having been at Bing Travel and currently at a travel-focused startup.

1. Both of you agree that the core intention of removing just plain bad flights is a good default for users since you're looking out for what most people would consider unreasonably painful flights. The difference is whether or not calling it "Agony" makes sense to most people. A good solution is to call out for new users that "we have removed flights with 3+ stops or out of the way connections. to see all flight options, clear filters" and remove the pre-set filter conditions.

2. I would agree with Durga here that "From.." sounds like a lead price and is normally looked up on in retailing with some skepticism. However, in the case of Hipmunk, because you are picking one leg, it makes sense since there is a wide range of pricing that begins with that base departure leg.

3. On Kayak, see a departing flight you like? Hover over and click on it and it'll now filter and show only flights with that departure leg so pages of results become usually just one or two pages all with the same departing flight. Maybe one way to solve this without a second click is to show all of the return options on hover over a departure leg on Hipmunk.

4. Durga's point is that for flights with multiple stops, it's useful to know actual time in air so for people who hate flying you can optimize your price-vs-fly-time tradeoff.

5. Agreed, you can do some basic grouping like most travel sites do with early morning/morning/afternoon/evening/night.

6. I've been thinking about this a bit as we work on our product and the pros of the tabs are: You can see a better layout of the information vs. the default display in a browser tab but the cons are heavier weight within the browser especially if your site has multiple views/layouts. Also, if you start creating too many searches, the tabs start breaking other elements of the layout. By default, you could make "new search" open a new tab landing on an optimized search page w/ your last search parameters pre-filled.

7. Agreed to a large degree but I can see how they might want people to know that there IS live help available, just not right now. Maybe put more useful info like "Offline - back at 8AM" or "Offline - Email Us".