@pdxasflyer - TripIt has can access the Google API to get your confirmations from Gmail automatically. You don't provide TripIt with your password for Google; rather, you use the Google single-sign-on function. You basically, connect the TripIt web-app to your Google account. You have full control from Google to disconnect it anytime.

I have all my flight, train, hotel, car, limo reservation confirmations go directly to my Gmail account,and TripIt automatically adds them to new or existing trips. I love TripIt, with a couple of exceptions. My only problem with it is adding recurring meetings on a trip. But, it works great all other times.

For everyone else, the Pro version is very much worth the $50 a year. However, I don't recommend you purchase the subscription through Google Play, if you are on Android. Go to the TripIt website and purchase the annual subscription there, then use the TripIt free app from the Play Store. When you sign it to your TripIt account, it will see that you are a Pro member and turn on those features.