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Are there reliable sites where I can find sites to buy?
What kinds of things should I check out about the site before I but it?
Check Alexa statistics and toolbar PR. Neither of these will tell you anything on their own since they are no indication of true traffic levels, but they begin to build up a picture. Also check domain age, search engine positioning for obvious keywords and the number of pages in the index.
Other than that, just take a look at the content and consider how useful it might be to visitors. If there are plenty of articles and good pictures, the domain may well be worth buying.
A lot of domains are for sale because the owner has discovered that they don't actually attract as much traffic or make as much money as expected. Hang around at various marketplaces (which I can't mention due to TOS) and you will soon get a feel for the types of sites that webmasters are offloading more frequently, and which are flooding the market.