Before I started selling on eBay, I bought many, many Snap-on tools on eBay. While there are a few purchases I regret, overall I ended up with a large selection of Snap-on tools for a fraction of the cost of new. My general rule was to try to pay 50% of new price or less including shipping. And I only bought tools in Very Good, Excellent, or New condition. With a price cap like that I got outbid frequently, but with a lot of patience, I gradually built my collection. There were a few items I needed to pay more than 50% for, but those were items that were a bit less common or in high demand, (like new F80 ratchets right after their release).
My 'regret' items were almost always due to my failure to properly read a listing, but I learned like every one else that if a listing does not say if a tool is not engraved....ASK before bidding. I also try to stay away from listings without clear pictures, (or stock photos).
I've seen every sort of crazy packaging, but I don't know why folks get worked up over poor packaging. Since it's 100% the seller's responsibility to get an item to the buyer without getting lost or damaged, the only one who can lose is the seller. Tools are a commodity, and as long as you look at them as tools, and not some irreplacable collector's item, if an item is lost or destroyed on it's way to you, it's not the end of the world. Most sellers will immediately make good, or eBay will force them to. I don't see a lot of risk of loss to the buyer.