That’s some good food for thought. Being honest with yourself is hard, but you really have to critically look at your car like you’re buying it, not as someone who has loved it and long ago forgiven its weaknesses.
Being an “APPRAISER” for 30 years, I’m gonna have to defend my profession a little. This month I looked at a ‘71 Skylark and a ‘67 RS/SS350 Camaro on Monday, a ‘59 Corvette and ‘69 Camaro on Wednesday, and a ‘69 GT350 and ‘70 SCJ on Thursday (fun week, they’re definitely not all like that). I’m confident looking at all of these cars, but I don’t claim to be the authority on any of them. At this point I have a pretty good feel for reading the market, and if you analyze the comparables, you can usually see value ceilings of some sort. Sometimes they’re obvious (the ‘71 Skylark convertible had five ‘71/‘72 comps with sales at Mecum/Ebay/Bat in the last year that were sold within $1000 of each other-$18k was the value and $20k was the place nobody was willing to go for that model, a non-GS Skylark convert).
There’s a wide range of skills and knowledge in car appraising-it isn’t regulated very much. Many modern appraisers are making a living on late model wrecks, diminished value and the like, and may not know anything about your vintage car. You should interview them and see what they’re about before contracting with them and spending your money.
It is worth seeking out a year and model-specific guru for some cars. When a seller can take $10k-25k of Benchmark/Thoroughbred equipment off of a car without 95% of people being able to tell, you need some skilled eyes to go over it before you write a check. Or to tell you how special and valuable these things are if you’re selling and maybe you’ve just inherited it from someone and don’t really know what you have.
I’ve had some appraisers in my area give stupid, pie in the sky values to people to make them feel good, only to have me have to uncomfortably (with great effort) bring them down to earth when later when they actually needed to sell. I definitely get that. But I think it is naive to think that appraisers who usually charge $300-500 have a tendency or need to “make you happy” but somehow marque specialists who have to get on airplanes, arrange lodging and charge $2500-5000 don’t feel a similar pressure. The last year/model specialist report I saw was almost $3k billed and had an estimated value range of +-$25,000 (!).
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