Liberals/Leftists: What presidential elections would you have started voting Democratic?

[SWE]

I think I'd be a pretty safe Whig/Republican voter for the first several decades of being allowed to vote in New York. Erie County was overwhelmingly Whig/Republican until FDR (our favorite candidate in history was Clay, who broke 70% against Jackson), so that's the sort of perspective I'd be hearing disproportionately, there's a good chance my family's economic stability would depend on JQA's American system, Jackson was a personality and style of politics I don't think I'd ever really respond to, and, for those early elections, I would have grown up watching my hometown burned to the ground in a war that seemed pointless, which I think would make me despise Madison and who I see as his ideological descendants in the Democratic party. I think I'd be the type of person who isn't really a doctrinaire Whig but is a loyal Whig nonetheless because Jackson man bad. And, while I don't want to pat myself on the back and assume I'd be way ahead of the time of slavery, I am from an area that was a hotbed of abolitionist activity and obviously would never have lived in a position where I benefited directly from slavery, so I think I'd at least default to being soft antislavery, probably getting negatively polarized as the southern voices got more extreme as we inched closer to the Civil War.

First election I'd flirt with voting Democrat in 1884. I imagine I'd hate Blaine and see him as a crook, and I'd probably grow discontent as the Republican party moved away from the party of reconstruction to big business. On the other hand, Cleveland was the hometown Buffalo guy with a good reputation as a corruption fighter. I think I'd pick Cleveland over Blaine, view Cleveland's administration as a disaster and go right back to Republicans with Harrison, who I'd view as a disappointment but still prefer to Cleveland

McKinley vs Bryan I'm a safe McKinley voter - I'm not voting Democrat after Cleveland's disastrous second term and Mikado makes an excellent point - I wouldn't see Bryan as a likable champion of the working man, I'd see him as a nutter who wants to obliterate my way of life. 1900 though is where it gets interesting - I think I would be a committed anti-imperialist and Bryan would win me over with his 1900 campaign. 1900 to 1916 is really dicey and I could see myself going either way in all of those elections depending on exactly who the early 20th century version of me is, but I think it's possible that I'm a safe D voter in all of those elections. 1916 for sure - Wilson kept us out of war. Either way I'd be a Harding/Coolidge voter after that - everyone was.

1928 is the first election I'm absolutely confident I would have voted Democrat. I was raised Catholic - I would love Al Smith and I would hate Hoover for embracing an anti-Catholic campaign, and I'd certainly feel vindicated in that hate when the Stock Market crashes. From then on, I'd always prefer the Democrat to the Republican, with the likely exception of Eisenhower, who probably wins me over through a combination of basing his campaign largely around ending the Korean War and being the guy who beat Hitler.

So I'd say 1960 in terms of having an unbroken D streak, 1928 in terms of when I'm confident I would be a solid D voter with minimal exceptions, 1900 in terms of when it's possible I'd start being a solid D voter with minimal exceptions, and 1884 in terms of when voting Democrat first becomes acceptable to me as an option.