I actually think it is normal. We see it on gun forums all the time. If he didn't think the guns, phones, etc., that he owns are better than other options then he would own something else. Same with you, me and everyone else. I know I wouldn't go out and buy something if I were convinced there was a better option.
I think everything you said is logical, and correct - we all make decisions that are best for us given a variety of criteria. (price, size, caliber, brand etc)
But, price is always a factor and "better" means different things to different people. When I bought my first 1911 I knew there were "better" ones out there, but I had a price limit. So I bought the best one I could get within that price limit and was very proud of the decision I made.
I disagree that this is "normal", in my experience the one-upper is usually the person who is not confident in the decision they made, so they are always looking to one-up the other guy. It's the people who are confident in the decision they made that just walk away and let that guy keep thinking what he wants to.
Let's face it, at any price segment there are no examples where one pistol is clearly and arguably "the best" - it's way too subjective because any of them could have an attribute that is best for me but not for you or the other guy.