Nice thought experiment.
A few points:
  • iphone even after turning off, makes the device findable may by transmitting bluetooth signal periodically to "find my" network.
  • I wonder, if getting KYC bitcoin first and then over tor swapping it for monero and then back to bitcoin and then doing a coinjoin would make it more untraceable and non-KYC.
  • Long time ago when I had looked into it the bitcoin ATMs, fees were very high.
  • Buying a new phone with cash from a small mom-pop shop may be more easier, that too with mask on, different gait, as it would not have trail of electronic communication if craig's list or something like that was used.
  • After buying the phone you could leave it alone for 6 months or so, so any CCTV footage of purchase may get deleted. It would be interesting to find out policies of for example Best Buy to understand how long they keep the footage. May be employees would know.
  • Getting prepaid sim seems easy, may be activation needs internet, starbucks, school or library internet could be used for that. They are usually not as tainted as tor or other VPNs.
  • Driving to a crowded place seems good for now, but with increased surveillance and AI advancements of so called "smart cities" it will be harder to travel maintaining privacy as years go by.
The last section "Happy Ending" was funny, as all these things are may be useful for planning a happy ending massage as well.
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