Most Conservative 2-term Democrat President

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FDR was not a two term President.

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I think honestly, Jackson was probably the most regressive and reactionary of any American President (even people like Buchanan and Pierce, who more represented stagnation than anything else). He represented the degeneration of Enlightenment-era Jeffersonian thought into thuggish demagoguery. The Democratic Party he founded - made up of the planter elite in the South, the crooked machines in the North and those state-level bankers who opposed the machinations of centralised bankers for reasons of personal profit - really started to ramp up a lot of ugly phenonomona that would take decades to be fully resolved (and some might say have never been resolved). The old idea of the Founders that slavery would wither away and die was tossed - now slavery was to be the new normal. Racism was not unknown in American politics - obviously - but not till Jackson and MVB did racist attacks on blacks become an acceptable and omnipresent part of campiagn discourse. (it's very worth noting that this era saw the first smatterings of what we would now call left-wing union sentiment. After the collapse of the old guild system that was practiced by the craftsmen and artisans of the Sons of Liberty etc, new Workingmen’s Parties sprung up in the urban cores, formations which were cooly recieved by Jacksonians and Anti-Jacksonians alike, and led to the former doubling down on aforementioned racist sentiment.)

 The old internationalist doctrines of the Founders, even the most "nationalistic" of them all, was also tossed aside for the sake of tubthumping nationalism, a motivation which led to his one decision that has any latter-day merit, threatening to kill the POS Calhoun during the nullification crisis. And of course, there was a very anti-intellectual aspect to his supposed anti-elitism which has reverberated to this day; his legacy in that respect is the gutter press and the minstrel show (a tactic which was quite karmically turned back on the Democrats with the Whig's ludicrous attacks on MVB).

Yeah, I think there is a good case to be made that Jackson was not just a madman, but the single most malignant President in American history in terms of his long-lasting effects. Everything that was good and enlightened about the Revolution found itself channelled into regressive aims: ethnic supremacy, mystical woo about manifest destiny, faux anti-elitism, deranged nationalism, strongmanism, and a fetishisation of violence and militarism. And every attempt to build a left-wing or egalitarian movement in subsequent years was weakened by the fact this charlatan had diverted populism to build his own deranged movement for the benefit of his own rich backers.

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I think the vulgarisation of liberal politics would see the Democratic Party fall ever closer to Indian National Congress style politicking. Basically all the worst traits of the HRC campaign ramped up.