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So, I wonder what computers or OSes that Doug has experiences with. What was the first computer that he first programmed on? Is there an old 8-bit computer system he has fondness for? Or programming languages that he prefers?

This was prompted from watching some youtube videos restoring old 8 bit era computers.
Ooh, good question. A lot of Doug's background is congruent with mine by virtue of his origins as an role-playing character, but he also had a wealthier upbringing than I did, with access to resources that I never saw until I got into college. And then there's the whole "accelerated tech" thing to consider in Warriors' World.

So... without doing any research first and making this up off the top of my head, I'd say his first exposure was to early personal computers in elementary school in the late 1960s -- WW's equivalents to the C64 and the TRS-80, with IBM's entry into the field coming along around 1970-72 or thereabouts and grabbing his attention. One of those would have been the system on which he wrote his first program, no doubt in BASIC. Like me, he probably still has fond memories of the TRS-80 (or rather, its WW counterpart).

By the time he was in high school in the late 1970s he was already cadging time off the VAX-equivalent on which his father's studio did its accounting (at least before they moved over to IBM PCs). That would really be the system where he started doing more than toy programs -- and as this was the same period in which his mutant gifts kicked in, the system where he first gained a complete and total understanding of everything about it, when he knew he wanted to be doing "computer stuff" for the rest of his life. This would make him a UNIX hacker during the Elder Days when the Tapestry was being woven, and possibly one of the first pseudonymous gurus. (He may even have contributed to the Distributed Global Index architecture which makes the Tapestry different from our Internet.) It would be this system that he'd consider his true "first" and favorite.