I don't think they really look at your itinerary much or give much notice within the US to be honest. I have had no problems with multiple stops, however puzzled looks and some gestapo airline gate agents trying to find me more convenient direct flights is a different story! :mad:

However, Canada was a surprise. Upon returning from YYZ-LCA first trip, I had to go to secondary screening and had baggage opened and about 28 questions about purpose of trip and why was I going back same route again in 3 days and who and where would I be in Canada should they need to reach me. Jeez.

But again, just remain calm and stay honest. They ask some of the same questions in a different format not to test your patience but to check if your answer differs or catch you in a lie.