Recently I bought a long sought after card, the Fan Club Magikarp. I grabbed a raw copy through a middleman from Japan and I was really nervous the whole way through. There were just so many points where I thought something could go wrong. I posted on the Japanese Pokémon collectibles FB group and someone replied almost immediately that they could source one in NM/M quality raw, which sounded almost too good. He also quoted a very reasonable price, but also didn’t include a 10% tax and had very little feedback at the time. He was only in the group 2 weeks at this point. I paid 2k upfront with PP goods and services while waiting for the rest of my funds to transfer from my bank. Then he says his PP has been limited and asked for the rest by FF payment, which was not happening, so after some back and forth we agree to do goods and services but to his fiancés account. So at this point I waited for a time stamp with the card in hand and then sent the rest. He then tells me the card looked better than imagined too so now I’m getting real excited. After a week she actually arrived in solid packaging and looking crisp. Surprisingly there is almost zero edgewear but there is a minor edge dent which I was aware of. Overall very happy and two thumbs up. Just surprised that it all worked out honestly. Now I need to decide where to grade it…
Anyone else have deals that worked out that seemed sketchy at first? Lol
Amazing card! I never made a sketchy deal for the moment 
Hmm, I try to stay away from sketchy sellers.
One time I bought an entire old label CGC 9 / CGC 9.5 Poncho Wearing Eevee collection ($2,000+) from a low-feedback seller on eBay before the authenticity guarantee existed. The listing suggested that the package would ship from Arizona, but it actually shipped from Israel. I was 100% sure that it would arrive with junk, and that I would have to contact eBay for a refund.
Long story short, the package arrived in ~5 days. The seller had declared the package’s worth at $50 for Israeli and U.S. customs. I opened it up, and it was the real deal. I was so relieved.
I’ve had a sketchy deal or two buying from people who are unable to accurately describe what they have but they weren’t really sketchy in the same way they would’ve been today. 
One of the sketchiest deals I’ve ever made was non-Pokemon related, where I had to bet $2500 on a deal before it was finalized with a person I knew was a complete asshole who I had worked on for several days for an object I knew I was overpaying for. It worked out though!
parking garage for a neo destiny box in cash, dude could have easily killed me. Before I was wise obviously
Looked for a possibility to get a mudkip signed in France and asked in a Pokemon group. Got a message from a random guy with just a few eBay sales and no reputation in the Pokemon community who offered me to take care of it if I just cover part of his convention ticket. (We all know how much some sellers wanted for autograph spots during mid of last year, so the low price was the first red flag). Another requirement was that I’d send the money only via f&f.
(Second red flag).
Since he even offered me to get a sketch if possible and also briefly talked to me about cool color combinations (to get appropriate markers if necessary) I thought to myself, “whether I now play the lottery for a month or trust in humanity comes out on the same”.
Heard almost nothing from him after I paid until the last day of the convention. To make it short: got my mudkip and everything was perfect.
Turned out that he just wanted to start a middleman-business and gain customers.
I got a complete PSA 9-10 skyridge holo set (no crystals) sent to me untracked from Sweden.
It was over ebay so it was mostly sketchy for the seller but it arrived no problem