UPDATE:
Our game plan was to take the ring to 3 local jewelers that buy and get quotes. Use the best number as baseline for when we go to Chicago next weekend...if Chicago quotes are higher than take the best one and sell there. If less, than bring it back home and sell to highest local quote.
I'll just type out her texts to me basically verbatim...
So I visited 2 jewelers today. My friend Deneen recommended someone who offered $2,800. I just left my original guy we bought the wedding band from and he offered $3,500. He also said he'd put it on consignment for me in the store for $4,500-$5,000 to see if it would sell and give me whatever the final sale amount is. He said it's a lot of look for that kind of $ that someone couldn't touch at that price if bought new. No obligations, I can keep it there as long/short of time I want to and if it doesn't sell he'll give me the $3,500 after all is said and done. He was really nice about it. Said it's a really pretty ring and he would like to see me get as much as possible for it. But he can only offer me so much upfront because he has to be able to make some money from it. He also said if I wanted to try Craigslist he would be willing to have the transaction happen in his store so no shady business went down.
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I more or less replied with....try one more local place to get that 3rd comparison number and then we have our number to shoot for in Chicago. If someone there offers in the $4K's than might be wise to just pull the trigger and be done with it. Also said the time and hassle with the Craiglist idea probably isn't worth it IMO.