Good questions, John. Lots of subsections to each question, and I'm a verbose dude, so you know this is going to be a bit long...
I think I'll answer one question per post.
1. A. There are two times that come to mind, though one of them isn't really a scam in the classic sense of the word. The first instance, which I think I recounted here before, was making deadstockshoes.com (FKA shoetrends) for a pair of 49ers Speed Turfs and never receiving them, nor receiving a refund. Where I went wrong there was actually not being a ****. I had dealt with the store before and they are generally reputable. I had known from experience that they are really slow to ship - they have very good prices though, so I just took that as a trade-off. I didn't worry for a while because in the past I've had items arrive 2 or 3 weeks after order. But, then I forgot about it. By the time I realized they never came, the window for disputing via paypal had expired so I couldn't file a claim. I contacted Ron and he said he'd refund me, but never did, despite several further attempts to follow up. The other time was actually the purchase of an inauthentic pair of Tiffanys. (I called them overrated in answer to last week's question and was purchasing a third pair at the time... kids, don't be like me, I have a problem!) Anyway, I wouldn't call this a scam, I just got fooled. I purchase a lot of items from collectors and consignment shops overseas and sometimes the communication is bad and I don't have complete information. In this instance I had no direct contact with the seller and limited pics. The shoes looked quite good and the price was good but not red-flag waving good. I went for it and got burnt. ...I'll have you know, they turned out to be very good fakes. I've seen worse fakes approved as legit in the LC thread on NT. Fact is, I could probably sell them and there'd be like a 85% chance the buyer wouldn't even know. But, I'm not that kind of guy. I go through clothes and stuff a few times a year and donate stuff I don't want or need anymore. There's usually a few pairs of kicks in there too - I just threw them in with one of the donation batches.
b. What did I learn from it? From the first instance, I learned to boycott deadstockshoes.com. I should have been more diligent, but in that instance it was really a shock. This was an established business that I had ordered from many times before. And, from the second instance, actually I didn't change my behavior at all. ...I say this as somebody being lucky enough to be in a position where this makes sense, but I'm willing to take chances and know that occassionally I'll take an L. Some of the best scoops I've made over the years have been from bad pic listings or whatever. Rolling craps once in a while is par for the course, but I've come up so many times that the spoils of victory far outweigh the cost of the defeats.
c. why is scamming so prevalent today? Well, the obvious part of the answer is that the knowledge quotient of the average "sneakerhead" has dipped drastically, while the hobby has gotten a lot of attention. So, you have dumber buyers and more people aware that it can be profitable to resell kicks. But, I'm not going to focus on that. I'll say two other things instead. One, and this goes back to what I said earlier about "barriers to entry," is that when this was more of an urban phenomenon, a lot of the people involved had "streets smarts" simply because of the nature of the participant in the hobby. The second this is that a flood of new technologies, platforms, and models for selling create a greater opportunity for potential scams - there are more venues for them. Fewer sneakers than ever, as a percentage of the "collectible sneaker pool," are purchased from established, accountable, regulated, brick and mortar shops. So, more of the stock exists in the ether where scamming is more possible. I'm not going to say the new generation is necessarily more or less honest, but technology allows more avenues for transactions to happen and an easier means of letting people know about it. ...It's like the younger kids doing dumb stuff on Facebook or whatever. We weren't any brighter than you, but the technology didn't exist to show everybody we know how dumb we were.