From the time I became interested in photography, the expense of photography has always been a barrier, either real or perceived. I liked photography when I was a kid, but spending my entire allowance one week to buy film and all of it the next week to develop the photos was daunting to a kid with so many interests. The photos I produced with my 110 Instamatic were in no way close to the goals that I looked at in magazines either.
I tried again a few times in my adult years. Film and developing was still a factor, but I did find affordable used SLR cameras and lenses to up my game. Still, nowhere close to the pro images that I admired. I proceeded anyhow, but the pace was slow.
Then, I bought a digital camera. The quality was questionable, but I no longer worried about the cost of film. I began trying new things without the worry of money. It was exciting. The Internet was new and just about any photo of any quality would draw compliments. Having a technical background, it was simple for me to make my photos available to the world. That didn't last long as hordes of photographers jumped on board and posting photos became simple.
Once again, I was just another amateur. As the bar for what makes a great photo kept getting raised, my interests waned. I thought that the hobby was really just a money pit if you wanted to excel at it. My focus on technical quality clouded my judgement for content quality and blocked my ability to simply enjoy my only artistic endeavor.
Others started posting their similar grievances. I came across the famous "A Lesser Photographer Manifesto". I found the ideas fascinating even though I do not agree completely with all of them. Better cameras do have their place, but not at the cost of hampering the ability to enjoy creating the art. The main idea of the post is that artists thrive on constraints and that high end cameras do not help. I disagree as I've seen some awesome photos that came out of high end cameras and would not have been possible otherwise. However, there is solid proof that a true photographer does not need expensive equipment so much as the need talent and a love for the art.
Consider that some of the greatest photos in history were taken with equipment far inferior to even the most modest cameras today. This fact alone should inspire you to stop concentrating on any lacking you have in the equipment you use.
I avoid many social groups that concentrate on the camera used. Some Flickr groups won't even allow a post unless you state the camera used, even if it's in the EXIF data. A person caught up in this stuff should self-inquire as to whether they're camera collectors or photographers. Nothing wrong with being a camera collector, but it's not going to produce more interesting photos.
Best advice I received for upgrading your equipment is to by better walking shoes to get to where the photos are.