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A fella *can* do some serious bargaining and get away with it... Never hurts to low ball the guy with a $700 offer, and leave your phone number. Eventually, they'll realize the parking space is worth more than the car...
Just this afternoon I happened to notice a nice looking '65 544 with a for sale sign, so of course I stopped... Looked real good from a distance, but some rust bubbles in the body near the fenders, silicon caulk instead of fender welting... typicle bad work. But straight and otherwise honest car. Good interior. But the girl was asking $4k for it. I told her I wasn't interested, but I knew folks that might be... but I also told her she'd be really lucky to get half her asking price. She listened and fully understood. Some folks just don't know...
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-Matt '70 145s, '65 1800s, '66 122s wagon, others inc. '53 XK120 FHC
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