I think it's necessary to distinguish between upgrading simply because it's the latest technology and is a 'cool' thing to do, boosts your ego and appears to raise your status among your friends and peers etc; ...and upgrading because the new camera or software overcomes the limitations of the old equipment which has caused some disappointment during your processing of images in the past.
It is the latter situation that has always applied to me whenever I have upgraded my camera equipment, or software such as Photoshop.
Let's take a simple example of dynamic range. Long before Nikon began producing FX cameras with enhanced DR, compared with their major competitor, Canon, I was experiencing frustration and disappointment with some of my Canon images when trying to raise shadows that contained interesting detail (to me), or detail that I felt made the image more complete.
I understood the processes of HDR and ETTR, but the fiddling around required to get an optimum exposure for a single shot, and the carrying around and setting up of a tripod for multiple exposures when HDR was a clear necessity for the capture of good shadow detail, was a distraction and a pain. It was not emotionally satisfying, perhaps because I'm not a 'gear head'.
If one takes the example of moving from film to digital, the same principle applies in a much more obvious way. If spending a good proportion of one's life in a dark room, developing negatives and prints in a cumbersome way, and breathing in noxious fumes from the chemicals as a side effect, is an emotionally satisfying experience for you, then it's quite understandable you would not want to make the transition to digital and deprive yourself of that emotionally satisfying experience that you could continue to have in a dark room using obsolete technology.
Fortunately, the attractions of life in a dark room never appealed to me. Long before Adobe came out with Lightroom, I began processing my old film with a scanner and making prints in a light room, which I've always thought is a much better and more satisfying environment than the photographic Darkroom.