Aside from what will be the most common issue is I need another computer (use a separate machine, airgapped, never connected ever), what holes are there in my strategy?
Why did you decide to write down your private keys, instead of writing down the seed phrase that Electrum generated for you? There are multiple benefits to using the seed phrase instead of private keys - easier to read, easier to type back in, harder to make a mistake, built in checksum, will generate private keys for all your addresses rather than just one, no risk of losing change, etc.
Thank you for your response.
I mis-typed... I *did* write down my 12 word seed phrase.
I will research how to boot Tails from a USB stick.