3) Time zone issues are challenging. Yes, RFC2445 has been around since November 1998, but most major PIMs (Outlook, iCal, Google Calendar, etc.) have only added iCalendar feed support in the last five to seven years and they handle time zone rules differently. As you might expect, big vendors change their implementations from one release to another, which making things even murkier. For example, Outlook supports floating time zones. Google Calendar initially did too, but then stopped supporting them in April 2009 without warning. iCal 3 for Mac works great with TripIt's calendar feeds. iCal 4 does not. In this environment, developers like TripIt (and the travelers who rely on us) have to choose between unappealing alternatives. We've been taking a wait-and-see approach on changing our iCal feed format since making a change prematurely could cause chaos for a lot of people.
As to your point about TripIt having crazy dropdowns for picking a time zone for a reservation, I agree! We've got some work to do. We're actively working now to refine all our data entry forms (a big effort that goes way beyond time zone selection) so hopefully there'll be improvement on this front soon. Will there be a shorter dropdown? Not immediately. But the improvements we're building now will save a lot of headaches for all our users right off the bat. Once implemented, they'll make it easier for us to consider fancier things like guessing what time zone your plan should be in, based on its location.
4) Maintain user defaults: Expand/collapse doesn't persist from one pageview to the next. You've pointed out a shortcoming of our service that annoys me and many of us at TripIt. We haven't chosen to address it yet because we've got a long priority list and it hasn't risen to the top yet. We'll get to it, but I don't know when.
5) "Why do you bombard me with advertising?"
Advertising is an important part of TripIt's business. We're passionate about the mission we're on to improve the travel experience over the long term, and we must generate revenue in order to sustain our efforts. That said, we are constantly working to deliver a great user experience that world-class travel brands can also participate in. If you're a Pro user, you see ads on the Web and in some emails (fewer ads than free users do), but you don't see any ads in our iPhone, Android, and BlackBerry apps.
I hope this helps clarify where we stand on the issues you raised. I'm happy to talk further. Meanwhile, let us know if you want to delve further into your Singapore Airlines issue. I'm grateful for your feedback, and appreciate your patronage as a TripIt Pro subscriber. We're working hard to continually improve TripIt, and your feedback inspires us to do better.
Will Aldrich
VP Product