The major mechanical issue I can see with the idea of playing as Andrew Jackson and playing through the decisions of his youth (and I’d assume, eventually) his political career is that for a player to buy into their MC, they have to be able to, in some way, justify their decisions to themselves. When the MC has an option to commit war crimes in Guns of Infinity, I give the player a justification for what they’re doing, something that would make the decision to consciously commit an atrocity into a rational one. The MC himself might be filled with self-loathing later on, but the player has to be able to sympathise at some level if they’re to keep playing.
I can do this because most people don’t know how the story ends. They don’t have the luxury of living in the 9th century OIE and reading about the consequences and effects that the Dragoon Officer or his compatriots have on the world. We do know how Andrew Jackson’s story ends - a fact which will be at the forefront of almost every player’s mind as they make their decisions, and one which will colour how they see the character they are supposed to be sympathising with.
Likewise, there’s the design issue of deciding how much control you give the player. Does the story inevitably end in a political career, with all that implies? If the player chooses to (for example) never leave home, what’s the point of playing a game about Andrew Jackson, as compared to any other frontiersman in the late 18th century?
Personally, I strongly believe that we should humanise “monsters”, as a constant and stern reminder that any one of us could be remembered the same way if we aren’t careful about the decisions we make. However, I’d recommend that instead of putting the player in Jackson’s shoes (and all the baggage that implies), that you place the player close to him: a childhood friend, a confidante, a neighbour: a way which allows you to empathise with a historical figure without necessarily accepting his justifications (There’s a reason why Traudl Junge was “narrator” figure of Downfall, and not Hitler himself). Not only do you free the player from the burden of playing someone whose actions may have done real damage to their culture and their families (let’s face it, I’d be pretty uncomfortable playing as a Kwangtung Army officer, or a Company Soldier in the First Opium War too), but you also give the player more freedom to choose how their own MC’s story ends, deeply entwined with Jackson’s as it may be, either as friend, reluctant ally, or bitter enemy.