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I usually avoid bashing Windows and comparing to Linux, but come on :
* 32bit libs in "SysWOW64" folder, and 64bit libs in "system32" folder ? Makes perfect sense (sarcasm). Same goes for "program files" folder, even if less troubling (but why do those need to be in different folders at all ?).
* Separate configuration locations for 32bit and 64bit (in registry) ? Who stores bitwidth-sensitive data in there ? And relies on the OS to handle the case when both 32bit and 64bit versions of the program being installed at the same time ?
* Configured data sources (ODBC) only working for n-bits program if configured via n-bits GUI ? I'd really expected better.
Compare this with Linux, where there a "/lib32" and a "/lib64" folder which contain the expected, plus a "/lib" symlink that points to "/lib64". All the rest (configuration , applications, etc) is in the standard (bitwidth-agnostic) locations. I've been using 64bit Linux on my laptop since 2004, and it allways worked just as well as my 32bit machines.
Of course I know why Microsoft does these kind of hacks : backward-compatibility. That's the price paid for proprietary software, which often won't issue any update once the package has been sold. And Microsoft has been blessing this behaviour by working around 3rd-party bugs in each new version of Windows. They've been doing it for at least 15 years, and can't turn back.
Pardon the pun, but the bazaar is much tidyer and well-kept than the cathedral.