I will admit that there are plenty of times that I would take the complementary gate-check if the airline would be willing to check it for gate pickup at my next stop. Aside from wanting my laptop, a book or two, and a change of clothes with me (the last one being superstition) I'm generally not too worked up about having the bag with me on the plane (and indeed, on a number of trips in the past I would take my "checked" bag with me through security and promptly hand it to the GA when I got to the gate for a gate-check...I was within my allowance, but check-at-the-gate was quicker than check-at-the-counter and it gave me a little more slack in getting to the gate).
For the record, I've only had a bag go "astray" twice: Once when I got IRROPSed onto one flight while my bag went on another, and once where I made a connection and my bag didn't. Considering that I only made the connection in question due to running through Atlanta (my flight from Toronto was delayed several hours; if not for the fact that I had left my phone in an Uber, I would have just missed the connection [last of the day] and done misconnect games the next day), I can't fault the airline for not getting it through.