When starting out, I would like to keep this definition as open as possible so we don't start off by flogging unsuspecting users with some pedantic definition of retro… at least until we see an actual encroachment of those "we didn't really intend this" problems in actual practice.
I like the general concept of Retrocomputing according to Wikipedia. Because of their ubiquity, I would suggest sticking to their example as much as practical. They don't put a specific timeline on the age of the equipment, but their descripton is somewhat suggestive of computer systems that are no longer widely in practical use, but are preserved mostly in the hobby and preservationist arena for their historical and sentimental value.
Retrocomputing is the use of older computer hardware and software in modern times.
Following that premise, I would consider a retro-system as anything that a reasonable person would not consider contemporary to what is modernly available.
…not considered contemporary to what is modernly available.
Contemporary does not mean "went out of fashion yesterday." I know that leaves things a bit fuzzy, but it's a start — bring us your Magnavox Odyssey and Commodore Pet questions; the original Xbox and Dell Optiplex aren't quite there, yet.
I wouldn't try and draw a hard line that says {x} years or older is okay, but the year after that is not. Such judgements are largely dependent on the type of equipment and how it is currently deployed (or rather, not). But I don't expect this to become the Super-User alternative to support deprecated hardware simply because an iPhone 5 is considered sort of old hat while Windows XP passed the sunset of support. That is not the purpose of this site.
I'll stop there. I don't expect to resolve this on day one (or in hour one, actually), but it's a scope that I would let develop organically and refine as actual problems start to occur regularly in actual practice.
Enjoy.