If you're not a US citizen, then go about it just like any other cigars. If $100 is your price point, then order a box, try it and see if you like it. Or order some fivers of a couple different $100/box cigars and see what you like.
But if you live in the US, then chances are you'll spend the $100 for a box, customs will seize it, then fine you alot of money, flag your SSN so you're given extra scrutiny every time you travel out of the country and have your passport scanned, and generally make your life hell. :0
It's not worth it. There are alot of really good cigars that are not Cuban. Wait for the embargo to drop, then have at it.
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