The last time I flew American I wanted to check one bag and carry the other, ticket counter said it would be $20 to check and I should just carry both and they would take the oversized one at boarding. It saved me $20 for checked baggage and the flight attendant saw my CV59 ball cap and I was upgraded to first class for free. I told her I wasn't active duty or retired, I had only given 10 years of my time, she said "good enough for me!" It was the best travel experience I've had in many years.
Now if it didn’t take me an hour to clear security it would be all good.