@Governor :-
Hmm..... Y'know, I'm having a job understanding this, I really am.
I've just this morning set up a brand new install of Bookwormpup64 on a 16GB USB 2.0 SanDisk Cruzer 'Fit' flash drive. Almost the first thing I did was to try the ArenaChess-portable, and.....for me, it fired straight up.
Almost every portable I have on the system works immediately, without any messing about. Roger's done his usual beautiful job with Bookwormpup64.
Now; I will agree with you on a couple of points. The reason why Windows installers for any app you care to name will work straight away is quite simple:-
1 ) The view is taken that most Windows users are dumb, non-tech-savvy, and need handholding all the way. And Microsoft stipulate in their guidelines that if any app is to be recognised by them, it must meet certain criteria, i.e., you click on it to launch and it just works. If your app won't meet those criteria, they don't want to know....
....but of course, there IS only ONE version of Windows in use at a time. Everybody's singing from the same hymn-sheet, so to speak.
2 ) Conversely, the view taken with Mac & Linux users is pretty different. The majority of these are smart, intelligent, tech-savvy and know what they're doing. Chess games comprise 2 main components, y'see; the back-end, or 'engine', that makes it all work....and the front-end, or GUI that the user interacts with. And since there's a bunch of engines, AND a bunch of different GUIs, the view is taken to let the users make their own choices & assemble things the way they want to.
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This is not to say that Linux devs in general - and OS devs in particular - aren't aware of the mindset of the steady stream of refugees heading our way.......indeed, enormous strides have been made over the last decade to make things as welcoming, easy-to-use & "friendly" as possible. But we aren't all the way there. Not yet.
I daresay there will come a day when there is eventually just one, single Linux OS.....to match the one current version of MacOS and the one current version of Windows. We seem to be heading that way.....but I, personally, will rue the day that comes to pass, because all individuality will have gone. And especially the time-honoured principle - inherited from its forebear, Unix - of doing just one thing at a time (and doing it as well as it can possibly be done).....
And RedHat - because many of their devs are also on the kernel development team - are utterly convinced that THEY should be the ones at the helm of any such future undertaking......guiding it, steering it and making & enforcing the rules that will doubtless be created to "govern" it.
Mike.