Here's a question, if a business accepts crypto, but not your favorite crypto, would you swap in order to support the businesses effort?

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Yes. If it's Bitcoin. Otherwise, no.

With so very few vendors who accept crypto at all, and since many that do simply convert to fiat, why would you be unwilling to do the conversion prior to a transaction?

Yes, but I'd always ask why they don't accept Monero directly as it is a no brainer.

Monero is the only coin that doesn't come with compliance costs for the merchant. They accept it like cash.

No expensive payment providers that need to consult chajnanalytics to potentially freeze funds or whatever shenanigans they have in mind.

In all seriousness, I only ever would recommend merchants to accept Monero and LN accompanied (maybe) by a conversion tool like Trocador offers it.

So the merchant only ever gets "clean" aka fungible digital cash that doesn't come with strings attached.

Compliance costs will fuck over any serious cryptobusiness if they don't do it right.

always do

depends on the currency. Some currencies I wont touch out of pure ethics or morals.

Do you have a shortlist of coins you are willing to use?

Depends on how private the crypto is. If it's like Monero or Grin, I don't have a problem. But if it's like Bitcoin without any privacy settings added, I'm walking out or paying with cash.