I saw that video too. I'm guessing dude wasn't a subscriber, because Hes is one of the coolest, most laid-back guys in the sneaker game, and you'd have to be a cold-hearted d-bag to want to rob Hes. However, I was surprised that someone like him, with that much experience with copping kicks, would fall for such a simple okie-doke like that one. Gift payments is one of the biggest no-no's in the game; you just don't do it, unless you trust that person implicitly. On to the questions (sorry guys, this is gonna be a long one!).
Question 1: Never been scammed, before I took a hiatus from the "game", or afterwards, fortunately. I've always been very careful with making online purchases (vetting the seller as much as possible, asking questions about condition (if used), making sure to get detailed invoices - no "shoes" as the description, and as a seller, only shipping to confirmed addresses, and never taking gift payments or making them). In regards to in-person meetups, everything has been good, largely because I am also extremely careful; I always meet at indoor, public places (Starbucks is my main spot), during the daytime, and always with "protection" (not saying everyone should do this; I am a responsible adult who, thankfully, has never had to pull my weapon; and believe me, I've been in a few situations where a less-composed person might have). I sit in a position where I can see the person pulling up (of course, I ask what they're driving before they pull up; I don't ask if they're coming by themselves because I imagine that might weird some people out), just to see the person(s) I'm dealing with. There's never been a situation where I felt uncomfortable (i.e. several people showing up, looking like they might have unpleasant motives), but if there was, I would just leave. I'm not trying to get into altercations at my age; maybe if this was 10 years ago, but those days are gone. When the meeting goes down, I let the customer see the shoes. Keyword: see. I'll let them hold one shoe at a time, but never let them hold both shoes, or hold the shoebox with the shoes in it. It's that simple. Just to be on the safe side. Some people might say "don't be scurred", but the thing is, I'm not doing that for my safety; if anything, it's for the other party's safety. Like I said, I'm not trying to get into altercations. I get in, and get out. After letting them see the shoes, I make sure to get the money FIRST before letting them have the shoes. Once you've let them see the shoes, it's on them to let you see the money. Show the shoes, get the cash and give the shoes, and that's it. If you follow those tips, things will go smoothly (for the most part; nothing is guaranteed).
Question 2: Selling drugs (mainly weed) during high school (no pun intended). I've never had to, nor would I ever, rob someone for sneakers/sneaker money. Do I regret it? I didn't think so at first, but after thinking about it for a minute while typing this, I have to say I do; while weed isn't physically harmful in any significant way, it saps the motivation right out of you, especially at that age, and it was probably the main reason why I applied myself very little during that time; the fact that I graduated on time was a miracle.
Question 3: Ever since I can remember (2nd grade is where my memories start; I have brief flashes here and there of moments before then, but for the most part, my conscious memory starts at 2nd grade), I was into shoes. Shoes, comic books, sports cards, video games, and sports was all I knew back then. Growing up, my mom was able to provide for us pretty well; not like kids in West LA or anything like that, but nice enough, for the most part (something which I'm still very thankful for; happy mothers day, moms of the world!). My mom always bought me and my bro a pair before the new school year, and usually another pair at the half-way point. I would sometimes get another pair at some point during the year, due to getting really good grades or, mostly, my mom making up for "disciplining" me and feeling bad about it. You see, I'm Korean; Korean parents beat the ish out of their kids, but they call it "disciplining" their kids. My mom would go at my older bro and me (mostly me though; I was the "bad" one) in the basement whenever we messed up, but she'd always feel bad about it, and would take us to the mall or Toys R Us afterwards. I'd always try to get new shoes, as that was my favorite thing in the world. Usually, it'd be more along the lines of Ninja Turtles figures or a couple packs of basketball cards, but sometimes I'd get lucky. I see a lot of people that say their parents would never get them Air Jordans because they were too expensive, but I guess I was lucky in that sense; those were my favorites growing up. A lot of times, I would make my brother get a pair of Jordans too, just so I could wear his shoes sometimes too (he was older, but I was always more the "older" brother). When his foot started getting bigger than mine and I couldn't fit his shoes anymore, it was a sad, sad time for me (Hare 7s are ones in particular that I remember not being able to fit; thankfully I was able to get a pair last year for the collection). Being that I'm an 80s baby, nobody was camping out for shoes back then. My aunt went to pick up a pair of Concords for me when they originally dropped, due to me having the flu and not being able to go myself, and the fact that she had to line up for them was unheard of at the time. Thinking that parents would line up to buy shoes for their kids nowadays for anything longer than an hour is absurd to me; my mom would've laughed if I asked her to line up for some sneakers; when she realized I was serious, she would've slapped me. Thankfully, as mentioned above, mom dukes bought me Air Jordans. Not to say that she would buy me any shoe; when the prices on Air Jordans/Nikes started rising, there were a couple times that she nixed buying a shoe for me due to the price. Sometimes she would fluctuate on what she would be willing to buy me; in retrospect, that probably was due to her financial situation being unstable at the time; some years business would be great, others not so great.
Question 4: I'd let them be a sneakerhead, although I would always make sure they were safe in whatever they were doing, and I would instill the importance of buying what you like, not following hype, taking care of your things, etc. I'd let my kids do whatever they wanted to do, as long as it wasn't harmful to them in any way, shape or form. Period.