Many people use the bag you are asking about and I will let them address its use. I'll simply give you my thoughts about air travel.
The airlines credit card will typically get you priority boarding (I have United and Delta) right after first and business classes board and yes you will need a minimum of economy+ on some airlines to carry anything on board. The key is boarding early particularly if you are in economy of any kind. If you are the last one there, Business class may not be enough. I arrived late once because my connecting flight arrived late and spent 24 hours in Denver because the overhead was full and I didn't want it going into the regular luggage system. It was a full size Boeing plane, priority boarding and frequent flyer status was not any help. The gate agent didn't care at all about what was in my bag. In my experience if you can talk to the stewardess, they are much more helpful but they cut me off before I could get to one. I now try and allow at least 90min to 2hrs when I have to make a connection particularly if I'm coming in on a regional jet which seems to have poorer on time performance at least out of Durango. Going to South America once even 2+hrs was not enough and I spent 24hrs in Atlanta as I missed the flight.
On the tiny jets and turbo props, I carry my equipment so that I'm willing, if necessary, to valet check it as you board and then receive it immediately after getting off the plane. Right now I use a think tank roll aboard (international unless I'm carrying the 600 as it will go in the crj700 overheads I've tried) with lexan (like used in a storm door window from home depot) backed with closed cell foam in the outer top pockets and between the sides and the liner (you can open this area on mine, not sure about current model, with a zipper). Everything is in a lenscoat bag or pouch and packed tightly even if I have to use clothing for stuffing. If I have any concern about it possibly ending up in the baggage system (valet not available as in Denver) I go with a pelican case. Right now I'm using the pelican BA22 with a trekpak insert $$$$$ but I have only one trip experience with it flying internationally (6 flights all together). Chose it because it does not have the steal me expensive equipment look and it is lighter (designed and sold as carry on bag for clothes). Otherwise a regular air weight pelican case $$.
Yes, I have insurance.
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