Yep I would ALWAYS carry them on.
Last time we flew ... on a non photo trip ... we were on such a small plane that they had no overhead storage and my bag was to big to fit under the seat.
They told me I had two options: gate check. or don't fly.
Ughhhh
I reluctantly gate checked my bags (something I would not have done if we were on business) and hoped for the best.
My camera backpack (lowepro) was FREEZING cold when I got it back with a small amount of condensation inside. My pelican case with my hard drive and MBP was fine, no temp or moisture changes.
I frequently check my lights and flashes in a big pelican case.
I would say that unless you have a rock solid waterproof case always carry your bag on.
I got lucky I think.
Pelican 1510/1514 from Amazon will do trick for you if you are in USA domestic flight, if you are flying international, look at Katabag Bunblebee that you could use it as a carryon laptop case. Advantage with Pelican is you will not have to worry just in case you need to check-it in. Only problem with Pelican is weight, on domestic flights weight of carry-on is not an issue on international flight it is big deal. Pelican is legal carry-on size for most airlines.
I use the Airport Security bag but recently purchased a Pelican 1650 and it's uhhh a bit larger than I thought! It's definitely durable. Its for check-ins. Will hold my flash units and probably 1 body at the most. I'd never want to check in both of my bodies.
uld always keep one on me, JUST in case. Also, my lenses come with me. When I have money for back up lenses, they'll fly in there. It's a very safe and durable. I will also purchase couple TSA certified locks for them.
But if you're looking to check in, must get Pelican. I would never want to check in my Airport Security unless I HAD to for a very small plane.