There is really only one key. Make sure the other party is ethical, moral, and truthful. That said, most seller are. A phone call can really help But even some honest sellers become hard to deal with when something goes wrong. So define the terms up front.
Whether I am the seller or the buyer, here are my terms: Ownership transfers when the merchandise is delivered to the buyer in good shape. The seller is responsible for any damage or loss that happens during shipping. Insurance protects the seller so asking the buyer if they want to buy insurance is a passive way of asking them to take responsibility for any problems that happen during shipping. I just had a deal fall apart to buy a $1500 pair of tubes from the UK, but when he asked me if I wanted insurance and I told him it was up to him, that he was responsible for shipping, he backed out.
When I am the seller, I keep it simple by including the cost of shipping in my asking price (you may do it different, but I like simple). I include whatever it will take for me to ship it safely. I use heavy boxes, sometimes wooden crates (but they are not impervious, especially if you aren't a woodworker) and LOTS OF TAPE. Inside use lots of packing material and make sure there is no room for movement. I've never had a shipping container fail ro protect the contents. And make sure the shipping lable has a barcode and is protected from weather. I always cover my shipping label 100% with clear tape.
Not this is different that requiring the buyer to pay for shippig. tat is really a part of the agreed price. taking responsibility for damage during shipping is different.
The other thing I do as a buyer is NOT to tell the seller how I want it shipped. If you do, you are assuming responsibilty if there is a problem--"but I shipped it the way YOU specified". All I ever tell a shipper is to "take your time, I'm in no hurry. That whatever time it takes you to prepare it for safe shipment."
Finally, I never try to change the way a seller does business. So many people "want it their way". The seller probably has a routine. And if he stays in his routine, things will probably go well. If you ask him to vary his routine, you increase the possiblity that something will go wrong. Just keep that in mind.
So you're thinking now that you weren't expecting a discussion of what happens after the sale but most of the problems you see posted on this forum are caused by problems after the sale and unresponiveness of the seller.
Jerry