I'm going to both agree, and disagree with what Ebok says. The vast majority of the time, you don't want duplicate playbooks, so if you want a simple answer, it's no. It's not the ideal situation. It's can lead to boredom and the points about it all becoming about kill shit and a whole lot of "doing exactly the same, but with a better roll" are spot on.
But, in special circumstances, it can be worked with. You can take characters in different directions, like the gunslinger who wants to look out for the little guy vs the heartless profiteer. Maybe a brainer who supplements her weird powers with being able to handle a gun or a vehicle compared to one who talks his way out when the maelstrom isn't cooperating. The starting stats, and choosing moves from playbooks option on level up will help set each player apart.
I'd only do it if the situation really called for it and it threatened the group though. The whole party wanting to be a heavily armed gun totting gang is better served with a gunslinger, a battle babe, and any other with a heavy tilt towards shooting things up (best +cool and hard stat option, sawn-off as handy weapon, barter for better gear as soon and as frequent as possible). There's no reason a savvy head can't shop around for an assault rifle or a hocus acquire a car. Consider custom moves, but be careful with balance.
Some playbooks duplicate better than others. Savvy head is probably the worst, but even then you could probably spice things up by giving them projects that require teamwork. Conversely, your example of hardholder would be one I think would work best. Two or more hardholders vying for control over a single large hold, each with their own fluctuating hold over the people can be an interesting set up for a game of thrones style politics, combat light game. I'd still think hocus and choppers would be better, but if they don't appeal to any of the players, why not multiple hardholders? There's so much to work with for pc-npc-pc triangles as you struggle to convince people that you're they should be loyal to. Do you go the fear route, or spend precious resources keeping them happy? Or up the scale and everyone has their own settlement, joined against a larger threat. How do you deal with an underling getting caught stealing from an ally? Make an example and piss off your own people, or show mercy and lose an important trade route?
Ultimately, the best solution is talking the the group openly and honestly to find out what everyone wants (yourself included) from the game.