Matt, I agree with you that estate sales, garage sales, etc. are probably the best place to make profits. I would disagree, however with your statement about not making a dime from ebay. I have actually done quite well on ebay. There are PLENTY of value buys there is you know how to find them and have enough time.
My wife would say that I spend entirely TOO MUCH time chipping and she would probably be right but I enjoy every minute of it. If I worked out the amount I have made per hour....it wouldn't be very impressive. BUT, over the past 2 1/2 years I have made enough to fully fund my 400 chip collection that I have spent $6,000 to assemble. I have about 400 chips that I have bought for resale and still own. I have taken a couple of trips to Vegas funded by my profits, paid off my credit card.... and still have (what I consider) a large balance in my Paypal account whenever chips become available.
Again, if I factored in the hours spent....it is probably WAY below minimum wage but when you enjoy it....who cares?
The important thing though as others have pointed out is that you have to know the market. You have to be patient and allow allow chips to pass you by if the price isn't right. And most importantly, you have to enjoy it. I have made mistakes though. I haven't made money on every chip for sure. I actually remember when I was first starting out, I didn't know who David Spragg was. He posted some chips on the boards for sale and I (feeling more knowledgeable than I was) tried to tell him what the chips were worth. After schooling me, I realized that this was the guy who wrote the book. Literally. . You can't win them all!
As an example, just last night I sold a chip for $235 that I bought for $15. This is not a typical profit obviously but over the past 2 1/2 years, I have had quite a few of them.
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