Both Craig's list and Facebook are hit and miss. Some people think that the item is worth so much that can wrap it for free in gold when they sell it. I grew up around some people like that. They either had the money or the time to sit and wait for that one special person to come along. At the same time there's still deals to be had. Recently came across a 3 year old 8" wide bed jointer that's $3200 new and with an asking price of $2000.
I don't look too often so my skills on finding deals has dropped off. I did start to get back into woodworking several years ago when auction prices were much lower. So I'm not really looking for any specific tool. But if the right deal comes along I'll upgrade. So if you've got some old stuff you want to get rid of you might as well try. But I don't think that high asking prices means high selling prices. If another stimulus check comes out that could change as people with free money tend to overpay.