@geo_c :-
I'm surprised you like the sound of my voice! I think I sound dreadful when recorded..... 
Yes, I do have a liking for "older" stuff. I missed so much older stuff when it was first around - due to life getting in the way - and I'm kind of re-discovering them for the first time. I also have a liking for seeing just how far I can push the envelope with older OSs, and am frequently surprised by just what many of 'em ARE capable of.
Also - though I hate to say it, and will no doubt be castigated for doing so! - I find that older Puppies are just so much more "fun" than some of the newer ones, despite being so quirky in many ways. That's part of their charm, as far as I'm concerned....

TBH, most of the older ones are kept 'safer' by running many of the internet-facing apps from a much newer chroot; browsers, natch; email clients, and various other bits'n'bobs. And it keeps them viable as daily drivers, since so many of us spend the greater part of our time on-line. I know I do; there's hardly anything that doesn't have either a web-app or online equivalent of some kind these days. The portables come in very handy for this, and usually just run from the chroot's /opt, with a relative link into /usr/bin; as for the host chroot 'launchers', I make use of and simply modify those provided by watchdog from back when he proffered the chrooted PaleMoon browser, at the time when Darry & I were playing around with his customized Puppy 4.3.1.1, the "Phoenix". Damn, that thing was fun..!
Most folks are obsessed with security, fixes & patches, and endlessly keeping everything bang up-to-date. With the ease of backing-up and restoring, such stuff has never really bothered me.....though as "staff", I'm well aware I'm not really 'playing the game' by recommending everyone to always use the very newest releases all the time. I have an install of the current release of BookwormPup, though I really haven't done much with it. I've never been a fan of Synaptic, and I see it still hasn't improved any. It may get more use over the next year or so. It almost certainly will, as browsers gradually get beyond my current 'workarounds' for older Pups. We'll see how it goes.
I use a Bionicpup chroot ATM for 32-bitzers (Tahrpup became Xenialpup, which then became Bionicpup), and a Fossapup chroot for 64-bitzers (Xenialpup -> Bionicpup -> Fossapup). I periodically upgrade these as time passes, probably every 18 months or so, so that internet -facing stuff stays somewhat more secure. For other apps, most of the native ones - if they work fine, and do what I want - I leave 'em the hell alone. If it works, why try to "fix" it? Bigpup says this often, and I've always agreed with his viewpoint on this.
As for highly-customized, well; I take the view that I'm the one who has to look at the things all day long, so I don't mind dolling 'em up with plenty of eye-candy, along with all kinds of shortcuts & easier ways to access and do things. Yes, I DO like my GUIs, and the more practice I get with YAD & gxmessage, etc, the easier it all becomes. It's amazing how often I find myself recycling the same snippets of code over and over again. They work, they do what I want, so.....I re-use 'em.
I'm a dinosaur at heart, I don't mind admitting it.....and to me, Puppy IS endlessly customisable, once you understand how stuff works. Barry really knew what he was doing when he picked ROX & JWM for a desktop combo. As a child of the early 60s - and a Sagittarian to boot! - what else d'you expect of me..???

Mike. 