I can only speak for myself, I would say in general yes.
I started off with a film DSLR and to be honest, due to cost I never really got into it in a big way. It was a Canon Powershot S60 that I really took a lot of photographs and learn.
The next camera was a Canon 30D and if you ask me did my photography improve? Hell yes. No more shutter lag, shooting through an optical viewfinder with much faster controls. It was like someone had taken the chains off my feet and wrists. I was able to for the first time really do what I want to do.
The next camera was a 5D2, this I guess was more an evolution, I am now able to get photos looking the way I wanted. The 30D lacks that depth of colour, I wasn’t able to push the files the way I could with the 5D2, this was immediately evident in my first wedding I shot with the 5D2. I still look back at those photos now and kind of secretly impressed with myself how good that looked.
After that I would say, still yes, my 5D3 had even better feel to the photos but these things are really something I’d notice. This was most evident when I had to shoot 1 wedding with 5D2/5D3 side by side. I remember at the time during the wedding I was much more impressed how the 5D3 was looking, I literally got home and ordered a 5D2 the next day.
5D4’s improvement felt less dramatic, sharper images with higher resolution, better DR and better focusing but I don’t shoot particularly different. I have bought other things that improved my work more such as lenses for the look that I want, flashes and even doing some work at a lower rate than I ought to have but I wanted the experience in order to expand and improve my portfolio.
These days it’s all much of muchness, I think I know much more now I would be able to compensate for most shortcomings of the camera. The hardest thing one need to learn is the limits of the camera you are holding. If you know it’s limits then you know what works and what doesn’t. This will then allow you to get the best out of it. If you don’t know it’s limits and never push it to its limits then upgrading the camera would not yield improvements.
Think of it as like a numerical ladder. If the camera can shoot in a range of 1-5 difficulty and you ever only push it to a 4, it doesn’t matter if you get a better camera with a 1-10 rating, you won’t ever use that extra steps of improvement and latitude that it affords you and your photography won’t benefit from it. i.e. if you are ever going to use the camera to shoot stock photos for Argos, ISO100, F/11, off camera flash, small websize JPEGs. It won’t matter if it’s a Canon 30D or the 1Dx2. The difference in quality between the 2 would be impossible to tell by anyone.
Side note – I think wedding photography really does push the gear to its limits in every way. In a single day you are required to shoot in every possible lighting conditions, bright midday sun, indoor dark with variable lighting, indoor with low light and no flash allowed, fast action shots, food photography, stills flowers photography, some product photography of gifts, portraits, candids, documentary, architectural shots of buildings, interior architectural shots, some landscapes, long exposures, there are even macro stuff sometimes of the rings. You will be pushing yourself and your gear at the extreme due to the nature of the work. You have to know the camera and its limits inside out, you need to know at what point that just won’t work at all so you need a workaround due to the limitations. It is in situations like these when you can objectively say “this camera is better” in this respect because the previous camera would not be able to get the same photograph you wanted. It could be anything from AF tracking, to being in a church and not allowed to use flash and tripod and it’s dark so IBIS can help.