Can't help you with most of that but my earliest trip with TripIt was March 2009. That is when I started with them so they have everything I have done. I don't know if it will go on forever, but we will see.

I have since stopped using them and moved back to Tripcase. This is mainly because the iPhone app for TripIt is very slow for me with the latest application update --- prior to that it was pretty solid. It seems more interested in loading the adverts than the data and the app is unusable until it loads. I know its a free service and I would shell out the $50 if I was sure it was fast.

I have used other apps that use the TripIt API to get the data and have paid for them so that might work out as well. There might be some like

http://www.silverwaresoftware.com/TravelTracker.html

they use the API so the data is available from TripIt and then can store additional information above that, they may be able to help and provide you what you are looking for. they've been accomodating to me with features in the past (not sure why I am not using them anymore. Note that each module costs (such as the app, then adding TripIt integration, then expenses, etc).