There's nothing with buying them used, but I would recommend buying them though headfi, since most members take good care of their items and is generally honest and modest about any condition flaws on the items.
It depends on where you purchase it from. I've had good experiences purchasing refurbished goods, but not all products labeled as refurbished are alike. I only tend to by "factory refurbished" as these products should meet the quality of what's sold as new as they're refurbished by the manufacturer or by one of their repair contractors, etc. I don't think there should be any problem if purchased either directly from the manufacturer or from an authorized dealer.
One thing to keep in mind is that a refurbished product has a very limited warranty period (if any), so that's one other reason for the lower price.
Refurbished would depend on whether it is an authorized seller or not. Check the main website of the brand you're looking for to see if the seller is authorized or not. Unauthorized seller resell returned products on their own, and the product would not be covered in warranty from companies such as Sennheiser.
It would also help if you check the seller's feedback, someone like Dakmart is infamous for their terrible customer services and their tendency of sending out broken products. It's best to be careful when purchasing items refurbished.
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