"He is a boy."
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No, writing Hebrew in Latin (not English) letters should not be allowed. That would actually be a downgrade, as you wouldn't be learning proper Hebrew.
You don't need to buy a "snazzy keyboard with exotic weird letters" - your computer already has the capacity to write in Hebrew, you just need to enable it in the language settings.
But my question is - if it's weird, why do you want to learn it?