Some of this may be out of scope for this subreddit but any help appreciated! I would like to try some gambling sites online that require a VPN and bitcoin deposits. Obviously my bitcoin purchase will be reported and the blockchain will have a clear record of my transfer to what is likely an obvious wallet for a website (could vary though). If I have any earnings I would send the bitcoin back to my wallet and potentially sell in the future, which would be reported to the IRS and a clear taxable event. I would file this on my taxes without a doubt as I know of no way around that.
What I am concerned and asking about though, is whether this will cause any issues seeing a potentially larger (we can all hope) transfer to my wallet and a sell of much more bitcoin than originally purchased. I would have obviously left a pretty easy trail from my wallet to an offshore casinos wallet and then my taxes showing me selling more bitcoin than ever purchased.
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