Pre-Dominiom war when everything is pretty chill. Starfleet kinda seems fun until you realize that you have to basically do military training and all this bullshit to join and then you gotta go die in space half the time. I'd maybe just try and get a runabout or the equivalent and just sorta wander around with some pals and look at totally safe and previously explored space things. I would also open a Volcel Precinct on Risa.
Fair play. I guess I'll just go with like, season 4 ish of tng for timelinery. Although initially I was thinking like, pre Wolf 359. When Starfleet was at its most Vibin'. You could just start the Maquis early.
The Cardassian Wars do predate even Wolf 359, though I forget by how long. The Wounded is so good because it establishes the fact that the dissent and dissatisfaction is already there, not just in terms of Cardassia, but in general
If you want to be on the crew of the Rutlidge be my guest. I am just kinda aiming for the less obvious 'fight' answers.
Also this is getting annoyingly pedantic.
I am a coward so I am not even thinking about fighting, more just helping outside the Federation, we see people like Kasidy do so
Hell yeh, cool space trucker who sometimes let's things fall off the back of the truck. That's a sick way to live and Kasidy Yates is a hero.
buddy you asked a hypothetical question about star trek, the pedantry is baked in