There is no way I can answer that. There are just too many variables and it is going to depend on the person and their situation.
$1,000 is a fortune to some people while others spend $500k on a fun night in Vegas.
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Perhaps it would be better if I rephrase.
If you are securing what to you is a fortune (however you define it), would you opt for the additional security (& complexity) of multisig, or as a non-public bitcoiner, would you feel comfortable with single sig + passphrase?