Bigpup, that sounds do-able for someone who upgrades a lot and has basic needs : browser, email, office suite, and likes to try new stuff and buys a new computer every couple years..
But for me, I find that to do the stuff I want with the equipment I have, I have already spent many hours finding workarounds in those programs, altering many deep settings (eg. in about:config in seamonkey), and yes delving into Wine big time with obscure CAD and CAM stuff. I find that upgrading often breaks the things I use because the latest dependencies or kernel modules no longer work or support old code or devices. Then I get sidetracked into altering kernels, etc. and end up with a custom puppy (when what I wanted was a stock version) with its own potential problems.
Likewise Wine itself stops supporting older programs, or older programs themselves can't be upgraded, or are no longer even offered, or have features removed or support only newer hardware, etc, etc. Upgrading in my experience especially lately is a multi-forked rabbit hole of troubleshooting and issue solving that a homemade custom sfs can't address.
The greatest force for unwanted upgrades is the commercial obsoleting of internet protocols and standards, overloading of commercial javascripts on every website, and consequential increase in wasteful bandwidth. These changes enforce demands for new upgraded browsers, which in turn require new dependencies, and those dependencies require new support devices kernels and faster processors and memory. And finally new OS versions.
Interestingly, the technical quality of what does eventually get through as images, video, and text on the Net is not improved commensurate with the massively increased need for resources. Most of the additional computing power is wasted on creating hidden user commercial dependency and targeting.
Anyway, I upgrade when I absolutely have to, not because I want to run the latest and greatest version of Puppy. I don't expect improvements any more in any technical capability for PCs -- computers and programs reached the level of my most esoteric needs probably about 5 years ago. I'm just trying to preserve those capabilities now, when supposed improvements actually threaten to erode them as a result of unrestricted net commercialization.
Let me just add, sure I do try out new pup distros, out of curiosity, and wanting to keep in touch with what our community is doing. But that's different than switching my daily work version.