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I'm curious what makes your experience so painful. I've found using Craigslist to be quite painless while selling or buying (Chicago, Paris, and SF) - usability is ridiculously simple and straight forward.

IMHO, KISS is part of why Craigslist has been so successful.

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Try keeping an eye out for certain models of older vehicles. I like old VW's but there is no way to easily say, "just show me Volkswagens made before 1980", it takes a query like.. (1948|1949|1950|1951|1952....|1979)

Now I have those bookmarked and saved, but for someone like my dad who also likes Volkswagens, he doesn't know thats possible so has to weed through hundreds of newer VW ads. Thus its painful.

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