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It will happen eventually. There might be a minimum level to make sure you don't get slaughtered but I'm not sure off hand. It didn't start happening for a little while in each of my games. I'm guessing the game won't send the assassins until you are somewhat prepared to fight them. It wouldn't be much fun if they cut you to ribbons because you had poor equipment and skills. Take note though, you usally rest when injured and the assassins will attack you at the start of your sleep so you might not be healthy enough to survive. IIRC, travelling to Mournhold stops the assassin attacks but you might not want this as the assassins equipment can be sold for a nice sum.
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