You start with Star Trek the original series. It’s old. It’s campy. Dated cultural mores. But it’s where the genre was birthed and sets the beginning for everything that came after.
Hmm...an intriguing take. I'll get it loaded up on my server (through LEGAL and OFFICIAL avenues) along with the next generation. So if it freaks me out I can jump ahead to TNG
It shouldn't freak you out. There are some parts that will make you say "What the..." out loud, though.
The biggest issue I had with TOS was the music. Get ready to quickly turn down the volume because some of the musical cues are shockingly loud compared to the rest of the audio.
Volume issues aside, I find that the music is far better in TOS. I am working through DS9 and the soundtrack is so pale and bland. It’s really the worst element of the show, but I like nearly every other bit of it. They just don’t focus on it at all.
For example, the fight music in the original amps the viewer up, while in DS9 it is barely noticeable. I prefer TOS in that regard.
I started with the original series about 6 months ago doing my first watch through, and I think it was the right call. There are a few references in TNG that only make sense after having seen TOS, which to me makes it more enjoyable. I'm about halfway through TNG now.
Another great thing about watching TOS first is it really gives you perspective on how Starfleet has grown as an organization over the years. The protocol changes, new alliances, old enemies, etc. There’s a great reference in one of the early TNG eps about the prime directive that makes more sense if you’ve watched TOS (or are a Starfleet officer).
I, admittedly, watched about 1/2 of Voyager first, but I recommend going through the franchise chronologically if you have time. There are some bad/tiresome eps of all the generations, so maybe check and episode guide if an ep gets boring to see if it’s skippable, but there are enough amazing TOS eps that I’m glad I didn’t skip that generation. And it’s great seeing the similarities and juxtaposition of the old and the new.
Good luck. The best episodes are timeless despite the cardboard sets, Kirk’s pervvy obsession with sex relationships between men and women, and low tech FX. The worst episodes are really really bad. But I hope you can laugh at the terrible as much as i do.