People have funny ideas about this.
I travel light and only take carry on even for extended trips, but that is because I am old and lazy. I am currently in the Caribbean with 1DS MkIII, 24-70 2.8, TS-E17, 11-24, 4x 600-EX-RT a 17" MBP and bits and bobs which easily fit in my carry on.
But a lot of very expensive gear, photo and video, is checked every day, all those video crews traveling the world are checking their gear and it costs a lot more than our stills gear!
Flight cases and Pelican style cases are all fine for checking gear, that is what they are for. Of course you need insurance too for 'just in case' but don't sweat checking gear it is done every day.
There are some work arounds for carry on weight limits I have used. I have a very light rain mac that has a massive chest pocket, I can put it on and fill that pocket from my carry on gear and then switch it back after weighing. Same with a photo vest (though I'd use my mac and not a vest!), don't forget it is the bag that is weighed, you can take stuff out of it and put it back in afterwards. Also I have taken my laptop out of the bag and rested it in front of the counter, had the bag weighed, then put the laptop back in it. Yet another dodge if you are traveling with a companion, check in at different times and don't get the heavy bag weighed, you can get a 'carry on' ticket twice for the same smaller bag of your companions just swap them over. Another work around, get your boarding pass on line and negate the check-in counter entirely. Very few airlines have scales at the gate, though many have sizers so watch your dimensions. On the subject of sizers, now so many people don't check bags the airlines and boarding agents are tougher on carry-ons especially when the flight is full, pay the $10 to upgrade to early boarding so you get overhead space. The gate crew will pull any bags with wheels that look close to max size but are much more forgiving for backpacks of the same size with no wheels.
Obviously all my tips come from the low end cattle class modes of air travel, I am sure others can give advice on 1st and business class travel where the restrictions and allowances are certainly easier to live with!