We recently flew taking our 'jogging stroller' with us and out of 8 possible times we were only allowed to gate check it once. This actually was a really bad move as it was harder when going through security (everything had to be unpacked and removed) than when without it even though it meant carrying our 7 month year old and ensuring the 2 year old and hand luggage made it in one piece.

None of this was in the US or on United, so is not advice about the carrier more our experience of doing it both ways.