Been looking online and prices are not inline with Hagertys or other valuation tools, see guys asking 40K for a 327 210HP, powerglide cars. Are these pipe dream prices or what they are actually going for?

 

Haggerty is replacement cost, meaning what a dealer would charge for a turnkey car with no known issues. Rag tops tend to go down in winter and up in spring. Project cars or cars rag tops that need some love sell highest right now. If a rag top needed to have the rockers replaced and its done right it is very pricey. Many none SS's have been scraped over the decades. Many have been repaired incorrectly so be careful on "good deals". Firebirds tend to be a little cheaper.

You can go on ebay and look at completed auction that sold. If the economy falls this winter it may be a good time to buy.

 

What Gorn said and I'd add that location has a lot to do with it as well,for instance you'll probably find a lot more for sale in sunny Phoenix AZ. than you will in rainy Seattle,Wa.
Supply and demand plays a role in price points.