Interesting subject, and also interesting because I was thinking of broaching the topic also, probably spurred on by the same reasons as the OP.
Here are some of my thoughts, many of which have already been said by others. Some new.
When someone asks what an item like a vintage weber kettle is worth, there is only one answer: What the market will pay. The interesting thing about the market is ... it is tiny. Very very small. Probably over half the market for vintage weber grills is right here. As such, the answer received here is often NOT consistent with the reality of what a person selling local might even see. The most true way to market a kettle is probably (and I do not say this lightly) eBay. eBay will capture most of the folks here, as well as most of the other collectors. The "easiest" way (and I can not believe I am saying this is "easy") is through craigslist, but the general market for a grill on cl is really a different population than a ebay or wkc audience. You have to 'hope' a collecter is in the audience.
Personally, the most I have paid for a kettle is I think $30. (that doesn't count new handles of course
) And frankly....that is what almost any weber kettle is "worth", except the outlying kettle to the outlying collector. It is mostly like any other used piece of durable equipment. 25 to 50% of new depending on condition. In fact, I will go further and say a BNIB OTG is not "worth" $159. I would never pay retail for a new weber kettle. My scale for a vintage kettle generally tops out at 50% of comparable new.
So the next time someone asks, I think I will say, "ask your insurance adjuster what a 33 year old charcoal grill from the hardware store should be insured for".
But then there are the "graills". And the thing with the "graills" is they are not the same for all of us, and further we do not attach the same value to them. This is where we have to be careful. There are 3 or 4 certain specific kettles that I would pay "inordinate" money for. However, I would never consider these their value, since it is likely that there is literally no 'market' for them beyond 3 or 4 people. I would also never use my figures to guide somebody as to their value. If they take the time, effort and money to market the grill and get that price by finding the perfect buyer, more power to them,
but it is not what the general market would pay. Just one last semi related thought. Because we are that singular targetted collector group, that collection of enthusiasts in one spot, I am seeing some issues with inadvertant/unintentional/perceived stepping on toes in terms of things like auction identification, bidding, etc. Nobody wants to steal someone else's find. But in the end, If you want it, and you know about it, bid on it. You are the market. You can not simultaneously try to acquire something you want as well as manipulate it's value and availibility. If it is posted, go for it.