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I worry both sides equally. Getting the keys and necessary info to them securely without risking exposure is one massive hurdle. Secondly, even with the info, they might face a steep learning curve with recovery, wallet software, and understanding UTXOs or whatever else, potentially messing it up under duress.
Do you worry more about the transfer method (making sure they get keys, descriptors, wallet info) or do you worry that they will be unable to figure out how to successfully recover the wallet?