So, how much of this has to do with inexperience? How much of it is plain old lack of cash (There was no way I could afford the Fender 4 years ago)? How much was because I trusted the salesman too much?
All of the above. ?
As we progress as players we learn things (hopefully), not only about playing, but also about the instrument and our own likes and dislikes. A lot we can get from others with more (or different) experience than ourselves, which is what makes places like this so valuable. However, there is so much info that it's impossible to learn everything all at once and often we are not ready for that info when it is presented to us. Also, as you have already pointed out, info one of us finds valid may not apply to another of us.
While aiming for what our heroes play is a good strategy when we start out, it's not always a valid approach in the long term. As we progress, our tastes change and we start becoming more of our own person as regards what we want out of our instruments, just as we find our own voice on our instrument when we start departing from our influences.