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Reality check: sometimes gear has to be checked. I've covered the same sports events as the TV crew who freelance for network television (using their own gear, not the network's)... the guys who check 10 cases of gear at a time, whose value reaches into the $100.000's of thousands of dollars.
As a photographer who flys often enough to know the gate agents by first name... not just at my home airport, but at a few connecting airports as well... I'm just another passenger as any and everyone else, no matter how delicate or expensive the contents in my bags are. If they say check it, and I have to get to the job that day, then there may not be another choice. Raising cain is not an option.
I pack accordingly... starting with hard, watertight mil spec cases (like Pelican, Storm, SKB, etc) with bulb seals, two step latches, and a breathable one way valve. These cases are blocked and padded inside assuming the case will be dropped 6 to 15 feet from the top of the conveyer belt feeding the plane's baggage door down to the concrete tarmac (I've seen this happen a few times when the conveyer isn't pushed close enough to the plane's fuselage, and the handler inside the baggage bay can't keep up with the continual feed of bags from the ground crew).
I carry on the gear CRITICAL to getting the job done in case sizes that will most assuredly be allowed in the passenger compartment of the specific plane I'm about to board. I research the overhead and underseat dimensions of the planes when I book the flight, and sometimes will alter my flight schedule to a different time depending on the plane typically used for the route.
I routinely fly the commuter jet series of Bombadier CRJ's and Embrarer's. I've learned exactly where and how I will stow my gear in a CRJ100, vs. a CRJ200, vs. a CRJ700, vs. a CRJ900, (as well as Embrarer 145, etc etc). When handed a tag to gate check my carryon, I always accept it, smile, and say, "this plane is a 700 right?" (as an example) and the gate agent will say "Why yes, you know your planes" and then I'll quickly tell them exactly where I will place each bag, with the absolute confidence that comes from having done it dozens of times before.
I pack the optional, extra, nice to have but not absolutely required gear and check it. Sometimes, my most valuable, expensive gear is CHECKED, not carried on. It gets packed assuming that it will be dropped, opened, rummaged through by TSA, and banged around by robotic luggage sorting equipment. One case I use cost over $1,000... just for the empty case.
Federal Express doesn't always get there when needed... especially on the weekend, even when paying for Saturday delivery. I've had a case sit in the (wrong) Fed Ex terminal all weekend, never get to my hotel, and I've had to call and have them shipped back home, unused. Shipping charge was over $150. that weekend. I have found it just works better for me to fly with my gear, not separately.
It boils down to a balance of risk and practicality. If I said "I will NEVER check my gear"... then that stance would certainly limit my opportunities to work the jobs where flying is the only practical way to get there and back within the time available.
It just takes a little more planning, a little more thought, a little more courage, and a little less reliance on any airline employee to take care or give a care about a bag. Not having that unrealistic expectation, I fly freely and regularly, not fearing to check gear, nor having to... once adequately prepared with advance intel about the exact dimensions of the plane I'm boarding.
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