How to buy and who to buy from
Be a specialist buyer "Books" is a huge subject area. To be reasonably sure that what you are getting is really worthwhile you need to put some time and thought into studying the subject, or else you will be sure to get stung. You'll see a "first edition" of (say) "Gone with the Wind", you'll compare it with prices of other first editions, you'll think "Wow! I'm getting a bargain!" and only later will you realise that it is a later impression of the first edition, or the first edition by a particular publisher, which appeared years after the true first, etc., etc.
You cannot hope to be an expert on every aspect of rare and secondhand books, so the sensible thing to do is to devote your main energies to certain specialised areas, and try to find out all you can about that area. If you choose modern first editions, for example, get Joseph Connolly's book on the subject. It will be well worth it in the long run.
Auction buying The first thing to establish in any purchase is what exactly you're getting. Auction sites are set up in such a way that there's a deadline for each item and, unless you change the settings, items which are closest to the deadline generally come up first. That is not the best environment in which to sit back and make a rational evaluation of what's on offer. Track items you may be interested in as soon as they come up for auction, not when the hammer is about to fall. If you use the eBay "personal shopper" option, eBay will let you know about things in your special interest area as they come up. For more detailed information on auctions, click here.
Reputable traders Auction sites have feedback on sellers, but it's not terribly helpful, since a lot of buyers and sellers seem to go for an unrealistic level of mutual back-patting, and for other reasons, which I go into here. From a practical point of view, most auction traders won't automatically issue you with a receipt (though a few do). A lot will issue one on request, but not always, so if you need one for any purpose (such as insuring your purchase), check with the seller first.
The orthodox advice would be, never buy from anyone who is not affiliated to ABA (Antiquarian Booksellers Association), ILAB (International League of Antiquarian Booksellers), or other recognised body with a code of conduct. If you want to be sure of getting a fair deal, then that's good advice. On the other hand, there are good books at good prices from unaffiliated traders. It's a question on whether you're prepared to take a risk, what sort of feeling you get about a particular trader, etc.
Ask the right questions Whoever the trader is, as an internet purchaser you're buying an item you've never set eyes on (except perhaps in a scan). I think it's only reasonable to ask a lot of questions. Click here for a list of technical terms used by booksellers, and questions to ask before buying. The online description is rarely complete enough for you to be able to make an informed purchase. Questions at this stage not only save disappointment later, but give you a chance to get the feel of the trader (efficient, friendly, cooperative - the kind of person you would want to buy a book from?).
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