I’ve traveled in my profession for 18yrs, flying somewhere between once a month to 30 weeks per year. I’ll admit, there are a lot of quick in-and-outs same day or next day, I won’t take my pistol, since I won’t have any exposure outside of customer sites or the airport, but on any multi-day/night trip where I’m in a reciprocal state, I take it. It’s a lot better now, since there are so many states which are reciprocal compared to 10-15yrs ago. I’d venture somewhere between 250-300 trips I’ve flown with my pistol. I’ve flown it 4 trips this year already.
It’s actually a considerable hassle, not in the “flying with a gun” process, but in the general sense of, “now I have to check a bag.” If I’m not taking a gun, I don’t check my bag, as I can get a week’s worth of necessities into a carry on. Two weeks of business attire if the weather is fare and I don’t pack site PPE. When I fly without a gun, I leave my house 40min before boarding time, drive 30min into the airport, pass through Precheck, and usually have time to get a bagel and juice without pushing time.
So I plan an extra 40min at the airport. I plan for 30min to check a bag in general, then plan 10 extra min to get through the process of educating the checking agent on their own rules. Considering my alternative airport time is about 5-10min, adding 40 is pretty long. I also plan another 30min to an hour, depending upon the airport, to collect my checked bag. They don’t come out on the carousel, so it takes as long as the carousel, plus check time. I’ve had time where my bag was brought to their office, but the dude responsible wasn’t there, called in sick or on a long smoke break, I don’t know, but it wasted two hours of my life waiting for another person to get there.
Another headache - which may have changed - if your bag gets mis-directed, instead of bringing it to your hotel when it arrives or consierge delivery back to your house if it won’t get redirected in time to catch you on your trip, as they would with any other mis-directed checked bag, I have had to go back to the airport to pick up in person. Not handy.
I keep a paper copy of the airline website with their rules, and of the TSA rules. I also have bookmarks of their respective sites on my phone, because a couple times in my life I have had that one know-it-all agent who doesn’t know, and claims I could have forged the prints...
With the exception of flying with long guns, I like to have my pistols inside my normal checked bag. Locked with a cable lock in a locked hard case. I have a standard plan for how I pack everything, such I can quickly remove and replace the gun case, but not have the pistol case in an exterior pocket, or immediately obvious if someone daftly opens my bag. TSA locks on my bag, non-TSA on the hardcase.