it REALLY depends on the area.
I'm sure if you lived in california, and you looked at CL chicago, you'd be like "why are those half price? could those be legit? might be worth driving out there for the selection"
If you lived in middle of kansas, and you looked at chicago, you'd be like "Man, what a selection! I see like one pinball a month in my area, but MAN are prices high in chicago!"
Honestly, I don't search my area. When I'm in the market for a new pin, I do a multi-city search on CL, check 4-6 times a day, I check pynball, I check this market, sometimes wait for a pinball show, mr pin classifieds, I check (another site I don't care to name) that you can sometimes get leads on.. Just have to be patient, know what your willing to pay, work hard to search for what you want.
Most frustrating thing about CL (which is often true in real life), dealing with idiots, a-holes, profit-hogs and the "slimy" sellers, dealing with people that can't type or spell or really know how to use email, or a computer, or the internet, but give them complete free reign to post as many ads as they want without filters, complete anonymity. It's equivalent to going back 20 years, opening the doors of a newspaper, and going "Hey, anyone that wants to post an ad, hop on a computer and start typing"