If I could speak the local language and know basic information about the era and place, I would join the Navajo people from whence 12.5% of my DNA originated because I identify with that the most, it's strong in me. I feel like a fish out of water currently. I would be so happy with them. In fact I was recently in Arizona and I wanted so much to join the Navajos but I know it doesn't work that way. You have to be born in there in order to assimilate.

And I'd choose a point in history long before they were conquered by Europeans. I don't want to deal with any of that traumatic massacre bullshit.

Oct 1945 to 1949.

I'd die pretty quickly without modern medicine, so I might choose the era with the easiest access to strong opiates to make the process less painful.

1920's Paris

If you're going back to before technology got good anyway, might as well always travel to ancient greece (preferably Athens, as they're a bit less violent).

I think the key to ensuring a successful outcome for yourself would be to pick egalitarian societies, because then you have the highest chance of not spawning as enslaved or lowly.

So something like the late neolithic Samarra in ancient Mesopotamia, or maybe one of the American continent societies that had democracy.

@hungryphrog
That's a difficult one. On one hand if I went to the early/mid Victorian era, it'd be pretty easy to re-invent some shit, and I wouldn't have to worry about having to re-learn reading in the local language, but on the other hand it's... the Victorian era.
Antibiotics isn't as simple as simply getting a fungus to grow in a medium (such as penicillin in cantelope): there can be bad byproducts that also need to be removed, and scaling up the growth to significant quantities can be a big problem. What miiight be easier actually is using viruses to kill bacteria, but you need access to good quality meshes. And industrialization also isn't as easy as some books make it seem.
I think I'd take one for the team and go back to some ancient mostly egalitarian (but still some excess goods to support specialists) queer friendly society guaranteed to not immediately get wiped out, and get them started on the scientific method early, and hope to butterfly/forewarn the worst shit away.

Florida in the 1300s

You didn't specify the calendar used 🤓, so I'll go to the year 1401 in the hijri calendar (1980 in the gregorian calendar)

As a gay man, maybe early empire Rome? Or even like early nomadic tribe times? Like, before there were institutions large enough to oppress people en masse. I'm sure there was plenty of gay sex happening as a nomadic hunter or trader.

Too Black for that bullshit; you might as well just kill me now