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 To add: 
Even the most basic first step with a non-ideal setup is fine. It's not important where one starts, but where they end up with knowledge and time. We should all learn to teach newcomers using a virtue we all preach: low time preference. 
 "it's a long answer, but let me add..." 
Haha jk...
You know your long answers are always appreciated.  
 It's not an answer to your question, but I would steer someone to Wallet of Satoshi (I know it's non-custodial) and Bitrefill. Or Strike and Bitrefill.

Most people want to spend money.  So let them know, that yes, you can spend bitcoin.

Allow them to realize for themselves that they don't really want to spend it. At least not all of it. 
 Safest computer in the world is one that is turned off.  Regardless of the software stack be used have it implemented on dedicated hardware or better a dedicated VM.  With the VM approach, it easy to back up the whole system as many times as needed and had off to love ones when you are no longer around. 
 I'd add that BTCSession would be a trusted tutor is my mind.