For the NYC Triathlon my plan is take the bike with Trico Ironcase and dump everything as a carry-on to my transition bag. Only the floor pump causes a problem. I can not put it in the case with the bike, has anyone had a problem with checking in a floor pump? And what are the odds of not finding my bike at NYC airport? I am thinking 50/50
There has always been a mechanics tent set up at the entry to transition - you can pump up your tires there and leave the floor pump at home.
Don’t bring your pump. I’ll have mine at the hotel. 
I’ve flown into Newark 5 or 6 times with my bike, never once had a problem finding it (which is saying something at that airport).
Don’t bring a floor pump - just hit up the mechanics tent.