It depends on the quality of the gear you have. Do you have a dedicated listening room? Do you own or rent? Do you have a garage? Do you live in a large metro area where cash and carry re-sale is possible?
The original boxes are nice to have but not a deal breaker when I buy used gear. If you don’t have the room to store the original boxes what other options do you have? Paying for storage is ridiculous!
If you try and ship the gear in anything but the original packaging and something is damaged, it is really hard to sustain a claim from the shipping company. Even with original packing these companies deny claims. It is getting worse with time.
I’ve heard of companies wanting $200 for replacement boxes and packaging, so it is worth trying to find a place to keep that stuff.
I live in an apartment, and don't have much space to keep the original boxes. I sold my last pair of speakers and subwoofer on eBay, but for local pickup only. I don't think it's worth it for me to rent storage space just to store the boxes.
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