Do you think little Ace and Luffy ever got into trouble that made Crocodile question if pirate life was any easier.
You mean, pirate life without kids? Because he's got pirate life with kids ;D
I think he doesn't have to question, he knows that. He knows he chose the harder option, but it's not a choice he regrets.
But I bet there are moments where he allows himself to regret it. Like if Luffy and Ace cause havoc in Windmill Village (be it getting chased by a wild animal that rampages through the village, or setting something ablaze because they decided they wanted to try cooking meat over an open fire, or if they "borrowed" a boat to circumnavigate Dawn and ended up in the middle of the ocean). He's not perfect. He loves his little guys but damn, sometimes he wishes he and Dragon had made the - to use Supernatural terminology - the hard choice instead of the heart choice.
Surely by now he'd be an Emperor of the sea, nay, king of the world even, locked into a passionate battle against Dragon who wants to free the world of his tyranny. But instead he has to listen to another lecture by Woop Slap about Luffy setting a box of bugs loose in the classroom and pretend that he cares.
