Cleobeach said:
Would something like this work?

http://www.target.com/p/brica-fold-n-go-...f66QaApfH8P8HAQ

Or this -

http://www.amazon.com/BayB-Brand-Infant-...YHVFKD1QHPY12PT

For example, one parent always carries the baby through TSA/C&I and the other always carries the hand baggage. That way you aren't burning energy with a constant back and forth about "who has the diaper bag? type of exchange. The same could be applied to safety.

Our land-to-boat and back again were limited to day trips, water taxis, some dingy trips, etc. but in those instances, my husband was most comfortable taking charge of our son.

His focus was 100% on our son and I backed off and didn't distract him with a thousand questions, advice, coaching, etc. about how he was doing it.

Is your son's PDF the type that keeps him face up? Ours had a pillow type flap at the rear collar area with a handle that was always firmly grasped.

Also, is a bright color? Those stupid blue ones should be illegal.