Legality of repeated Western Union cash pickups?

Correct, a lot of cuevas now, in addition to trading USD -> AR$ they will also trade crypto such us USDT or USDC against AR$. So yes, it would be very simple for you to do. Keep in mind though however, that digital currencies incur a commission right now, and it varies on a daily bases.

so say you have 1000 USDT you want to convert to AR$. First they would deduct today's rate of from USDT 2% say, to end up with USD, then they buy those USD at dollar blue (compra). to give you an idea, depending on where you go the USDT rate is anywhere between 2-3%. I hope this helps.
Thank you very much. Much appreciated.

If I understand this correctly, I first pay +/- 2% to convert USD to USDT/USDC; then is a further fee to convert USDT/USDC back to USD (say +/- 2%), and from this USD to get the ARS there is then the blue rate (which is typically a bit lower than the CCL based rate at WU) [let's say this is another 2%].

As I see it: for me it is much efficient to go with the WU (if the above calculation is more or less correct, then this is about 6%; as I pay almost no fees for WU from Europe)
For larger transactions I pay around 4% to get my hand on USD in cash here (payment to a USD account, and collect here USD bills). So also for these kind of transactions there doesn't seem to be an advantage going crypto.

Anyway: I will try to do a crypto transaction in the near future just to get familiar with the technology. (I don't believe in crypto as a long-term asset, but see potential benefits in making transactions more cost efficient)
 
How do you know that you are blocked from WU?

i just tried to do another transfer, but the available money to send is zero “you cand send 0.00”. I didnt get a message or email from WU. Not sure whether this is temporary or permanent.

traditionally, i sent to myself ca 1000 usd (cash) and 2000 usd to my wife (bank account). Over the last 5-6 weeks i sent much more (ca 12k usd), mostly cash pick up. I might have overdone this …. The strange thing is: if i were to deposit cash in a WU location (and not from my European bank account), i still could do a transaction….
To give you an update on this message I sent a few weeks ago: a couple of days later it was ok and it has been working just fine again
 
If I understand this correctly, I first pay +/- 2% to convert USD to USDT/USDC; then is a further fee to convert USDT/USDC back to USD (say +/- 2%), and from this USD to get the ARS there is then the blue rate (which is typically a bit lower than the CCL based rate at WU) [let's say this is another 2%].
Coinbase lets you buy USDC 1:1, then you can withdraw directly to the cueva's address with a minimal network transaction fee. You do not need to convert it back into USD. You do get essentially the blue rate though which is a bit lower, yes.
 
Thank you very much. Much appreciated.

If I understand this correctly, I first pay +/- 2% to convert USD to USDT/USDC; then is a further fee to convert USDT/USDC back to USD (say +/- 2%), and from this USD to get the ARS there is then the blue rate (which is typically a bit lower than the CCL based rate at WU) [let's say this is another 2%].

As I see it: for me it is much efficient to go with the WU (if the above calculation is more or less correct, then this is about 6%; as I pay almost no fees for WU from Europe)
For larger transactions I pay around 4% to get my hand on USD in cash here (payment to a USD account, and collect here USD bills). So also for these kind of transactions there doesn't seem to be an advantage going crypto.

Anyway: I will try to do a crypto transaction in the near future just to get familiar with the technology. (I don't believe in crypto as a long-term asset, but see potential benefits in making transactions more cost efficient)

The price you pay to obtain USDT or USDC or whatever crypto currency you decide on buying depends on where and how you buy. Presumably, if you are buying in the U.S the fee is either 0% or 1%. I don't know what the prices are in Europe exactly to obtain crypto. I believe it's significantly more expensive. The 2-3% price I was referring to is here in Argentina, when you convert from USDT to USD.
 
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