The chess sets in my collection are mostly ones that I picked up for cheap at thrift stores. Each one that I buy has some "pro" that sets it apart from all of the others (e.g., vintage, size, style, portability, etc.) but then also has some flaw that makes it less than optimal (e.g., the colors of the pieces are too similar, the shapes are not distinguishable enough, a pawn is missing, the king has been chewed by a dog, etc. - there's usually an obvious reason why it was donated to the thrift store). I usually refurbish the sets as much as I can to make them usable, and sometimes give them away to people that I know will use them.
I haven't yet graduated to the really fancy sets (the most I've ever spent on a chess set is $35), and my wife makes sure that my hoarding doesn't get out of control. A new chess set coming in the door typically means an old chess set has to go out the door.
I don't know what it is about chess sets. I've always collected something (e.g., toys, coins, etc.) - there's something about the thrill of the hunt and occasionally finding something rare/unique at a bargain. I guess this is just another one of those things.
In my case I started searching for an old nice set and board when I began to play chess. If I would know what would happen I would perhaps go to a shop and buy a beautiful tournament set and board, a smaller board for analysis and a digital clock. I am not sure if this would be great or bad.
My “search for s nice board / set” ended with me purchasing all kind of things related to chess. Colleciting is something funny. You are basically hunting / gathering. You can of course with the time be a specialist, knowing all kind of things about the history of chess, having a website or publish books or articles about the topic. But actually you are not more and not less than the hunter/gathered, perhaps with an intellectual touch, perhaps only to justify the amount of money you spent with this hobby.
Yes, through your activities as a collector you can assure that some very nice chess items will not land in the rubbish. How many museums were build up with the things found by avid collectors? And I can imagine worst ways to spend money, like buying expensive cars every year.
And you can even make a business out if your hobby, buying and reselling all kind of chess related things.
What is your story?