I agree that the speed at which TripIt implements fixes, new features and improvements to their interface is poor. I have some features that I requested over a year ago which also seem to me to be obvious and easy to implement. I am sure there are many other people who are also making requests/suggestions so TripIt does need to filter and prioritize. But in some cases I don't understand how things got implemented the way they are from the start.... it makes me wonder if the people at TripIt just don't "get it".
I've been pretty impressed with some of the competitors to TripIt which I've seen emerge in the last six months. (Or maybe I only learned about them in the last six months). TripIt had a huge lead, but these competitors are cheaper or even free, and offer very similar functionality. If TripIt do not get their act together soon, one of their competitors who "gets it" will push them put of top spot. Let's not forget what google did to yahoo...