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Mac & iCloud Security

Hello, all.

First off, I do apologize if this isn't the place for this post. It's the best I could think of.

So, I will (likely) have access to a target's macbook for a few days this week and have a good idea of what the password may be since acquiring a few dumps. I'm a PC user myself so I just want to make sure there isn't some sort of Mac security problem I might run in to.
So if I were to log in and go into the iCloud's data, is there some way or notification that the user will receive on their iPhone? I assume since it is a personal computer that they wouldn't have to do 2FA every single time they went into iCloud on it.
And secondly, is it safe to just stick in a thumb drive and copy data? Or should I be mindful to delete say, a history of hardware of something of that sort?
I know that if I go into iMessage that the target will get a small bubble on their imessage icon on their phone, but I would do that when the target is asleep and would expect it to be gone once I'm done.

Please pardon me for being overly cautious. Long-time target here and I finally have my chance.


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