Oct 15, 2017
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If a friend of mine starts sending me money via Western Union (between $500-1000 a week), are those transactions going to be reported for tax purposes? Just curious if I need to be concerned about a paper trail catching up with us, or if 1000 a week isn’t really enough to turn heads. Will our IDs be recorded by doing this? He lives about 1000 miles away so we’re looking for the most private way to send money without it coming to bite me or us later on. Realistically we’re talking about two $500 transactions per week. Am I just overthinking this?
Which country are you from and why don't accept the funds in Bitcoins?

The US. If I accept it in Bitcoins, would I not have to deposit the converted funds into my bank account in order to receive the cash? I know basically nothing about Bitcoin, so forgive me, but I’d just like to avoid having a record of the money being sent and received if possible. The idea of a money transfer seems attractive because it’s just cash being sent and cash being picked up.
Western Union asks ID when you go to withdraw the cash. I gone to WU just last week and the guy behind me collected about $100 and he too gave his ID. It's a rule and we can't do anything about it. What you can do is, buy a fake paypal account and exchange your bitcoins for paypal and then ask the exchanger to add a note to the transaction like "for web design" or something along those lines.

As stated clearly in https://www.westernunion.com/ie/en/receive-money.html :

Visit an agent location near you with your government-issued ID.

If you want to bypass bank, you can buy prepaid cards with your paypal funds and withdraw it on ATMs.
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