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I have a number of items (among them, old (80s) Apple memorabilia and a nylon flag that's about 2m², featuring the Cupertino font).
I'm thinking of selling these (possibly in conjunction with some Apple-related anniversary), but I've no idea if they're worth $5 or $5000 — and I'd hate to guess wrong.
So how do you determine a reasonable value for such items?
@RobertCartaino, @Chenmunka, thanks for the way you have moderated this.
Here's a picture of the flag: 
Part of the value of any item is the demand for it. If there's no demand, even if there was only one made, it's unlikely to sell for a high price. You have a few options.
Scan eBay/Google Shopping/Craigslist for any equivalent equipment. eBay has a great feature that lets you filter your search results by completed or sold listings (there is a difference). Using those options you can see what people are listing items for vs what they're actually selling for.
Find an expert. You might want to look on reddit or other specialized Apple forums for people who might know about these things, or would be interested in buying them.
Ask Apple. This is more of a long-shot, but I've found that some companies actually value when people contact them about old promotional and collectable items. Hell, Topps threw away most of their trading cards from their early days and even they don't have a complete set of their catalog.
Another thought (mostly related to Apple). Have you ever heard of RedLightRunner? It's a site dedicated to Apple memorabilia. They have some items for sale as well as a near-complete catalog of other items.
I would guess there is a much smaller market for memorabilia in retro computing as there is for hardware - Things you can use your flag for are somewhat limited - A piece of (working) hardware promises basically unlimited fun. On the other hand, non-hardware stuff has generally much earlier met the dustbin than real hardware, so it should be considerably more rare.
Price for non-hardware stuff is definitely much more based on meeting the right buyer in the right buying mood at the right time. I, for example, have a quite decent retro collection, but have never thought (and don't think I ever will) of spending money on anything else but hardware. Just blatantly assuming everyone else might be like me, I'd say the typical retro computing guy will consider such memorabilia a nice side dish, but not the main course he would be spending considerable money on. You are searching for an Apple memorabilia collector, not a retro computing hobbyist.
In case you want to sell - I guess neither eBay nor auction houses would be the right place - Material like your example are too rare and too specialized for selling through generic channels IMHO (It definitively doesn't hurt looking, but don't have high hopes to get real guidance from there). Better try and ask in specialized Apple retro forums - a lot of them have "for sale" areas - whether someone would be interested to buy and what they would be willing to spend. I guess the proposal to try and contact the original manufacturer is a very useful one as well.
Ask an expert has to be the most obvious answer, and maybe sensible for higher value or rarer items. An auction house should be able to help (for a fee), although they can equally get these things quite wrong.
