The realization that we're headed to 1888 and not 1988 is a bit of a tonal whiplash to say the least. Genuinely not sure that even if you became a very wealthy individual then, that your quality of life would actually be better than a 2020s wage slave even despite everything, but there's something idyllic about a more disconnected life after we've seen the inverse. I believe there's still a chance to come out on top.

Pretty basic plan I think, but I feel like writing -

Location is the first question I think. I'm on the East Coast in the US, so I'd have to pick between an established city (I'd have a familiarity advantage with Philadelphia, but also NY, Boston, etc) or heading west. Not RDR frontier west, but still somewhere more up-and-coming at that time, a midwestern city like Chicago might afford more of an opportunity to make a better life vs. more somewhere with higher competition, I think.

I did just ask my girlfriend, if given the choice would she go back to 1888 with me or prefer to stay here, and it seems she and her personal effects are taking up some of the truckbed space. Someone to commiserate about the situation with is a tangible benefit though, you might find love there and settle down like Doc Brown, but I think it would get lonely in a way and affect you mentally having zero connection to your old world.

If you discard infant mortality, the average person actually lived to be about 70ish at that time. I would have to plan to be alive through the 1920s or so. With respect to that window of time, I'd spend part of this week doing reasonably thorough research on local politics, economics (obtaining stock exchange data and looking into how you'd even participate, is a big particular focus that might make all other plans moot), obtaining relevant maps etc, reading on what daily life even looked like, just becoming as close to a general expert as possible as to what the big picture was in the late 19th / early 20th century in this city, with the benefit of all this foresight. I'm also wondering if there are near-future-to-them inventions, medical items etc that haven't been invented yet, that I could bring and capitalize on, this all falls into the research category. One of my trunks might partly / fully contain these types of books / downloaded+printed data.

Along that train of thought, blending in and not seeming like a time traveler / witch is an important thing I think. Showing up in period accurate clothing goes a long way, it might not need to take up too much space, but a couple outfits would not hurt. Maybe some looking into speech patterns of the time. That would take some prep though.

Starting money is an interesting question, showing up broke is not ideal. Carrying contemporary US currency wouldn't work. My bank accounts today are useless in 1888, so I would drain everything and start buying old coins I guess. Paper currency from that time is prohibitively expensive now, but I'll have to take whatever I can get within less-than-one-week, and presumably have more money now than I'd be able to spend on old money in a week. As much as possible, rush shipping online, calling around and heading to niche stores etc. Morgan Silver Dollars and things of that nature seem somewhat more available. $1 at that time is about $30 today. I don't have a good idea as to how much I'd be able to accumulate while still saving time for other preparation, but I think that it realistically could be enough to secure good lodging and starting investment money etc.

I think everything above will take a preponderance of my prep time. I should still have a little bit of space in the truckbed though. After some personal mementos, I'm looking into modern amenities that would be usable back then. There's a 3D-printed fully functional solar powered Gameboy that exists for instance, it kind of looks like it sucks, but with a flashcart with every ROM, I dunno there are worse ways to live. Some type of durable MP3 device would be great, etc etc. If I have room, I'll probably bring a guitar.

I guess my plan really involves this stock thing going well. With 40+ years of data in my possession, I fail to see how too much could go wrong, unless my impact becomes so great that it affects how future trading syncs up and makes the data unreliable. By that point, in theory you're one of the wealthiest people in the city though. Best case scenario, me and the Mrs. can get a mansion in the hills with a bowling alley in the basement, like Daniel Plainview in There Will Be Blood. Worst case, I'm very wrong and have to get a more normal job, but we still can live out a relatively peaceful life I hope. Maybe I use the guitar to see how people then care for the sounds of the Beatles or something.

Anyway- good thought experiment, thank you.