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Comment Re:And no more EasyTransfer! (Score 1) 860 860

10.1 -> 10.8: you can't, mostly because the processors changed with 10.4/10.5, and PPC got dropped in 10.6. However, had it not, the sequence goes like this: insert 10.6 upgrade disk, upgrade to 10.6, run app store, upgrade to 10.9. That's it, and yes, it would work, barring the hardware shift. on Intel macs, going from 10.4->10.9 works exactly like that, unless your hardware isn't 64-bit EFI.
Debian? sudo apt-get update && sudo apt-get distupgrade about 4 times? I took a machine from Ubuntu 7 to Ubuntu 13 that way with a few hiccups (mostly networking driver and netatalk related).
Just saying, it is at least doable, barring actual hardware-related reasons. With XP->7/8, it *should* be doable, but they made a decision to not support upgrading without deleting all of your files in the process.

Comment Re:Sundog did something roughly similar back in 19 (Score 1) 509 509

I loved Sundog, had actually bought the apple II version, and was so immeasurably frustrated trying to make a backup of the disk when I was 15. Now, it all makes sense. Can't post proof, of course, but I still have it in storage with my apple IIe. :)

In any problem, if you find yourself doing an infinite amount of work, the answer may be obtained by inspection.