I have been using TripIt for more than 4 years, and the last 3 years as a Pro subscriber.

There are two great features of TripIt: ability to automatically parse confirmations e-mail to create the itinerary and events; SMS notifications about delays and gate change.

Good things:
- The parsing is great and very little need to manually edit it
- Notifications for gate changes, delays, connection informations are really useful and saved my ... a couple of times
- The individual item are well presented

Not so good things:
- They are playing with the overall interface and some changes are backward (the current new beta account homepage for example: it has much less informations)
- Very complex ititnerary tends to break
- Bad parsing of AirBnb: TripIt can not see that multiple emails relate to the same stay