I can’t even begin to imagine the potential confusion of watching in chronological order, given how many timeline shenanigans take place.

An interesting experiment if you’ve already watched everything, perhaps, but if you’re just starting out then I’d say just watch in release order.

I recently had to think about this when a friend asked about which show he should buy on DVD to start.

I had to think quickly because he asked me while he was in a store that has a lot of complete TV shows on DVD/BD, and needed to know before he left.

After thinking for a few minutes, I decided to start him with TNG and continue in release order. TOS is just extremely difficult to look at and take seriously. I’ll have him get to it probably after the 3 “golden age” shows. Give him a reason to like the franchise before dealing with the old look.

So we’ll circle back to it for sure, but I want him to like the show.

What ever floats your boat. I watched them at random. I started with the original series and then movies to star trek enterprise with Voyager and then deep space nine and next generation.

Somewhere in there I watched the movies.

I once tried watching them in in-universe timeline order so it meant watching TNG and DS9 at the same time and then DS9 and Voyager. I didn’t get far into it before I decided it was a bad idea.

So now I have just done a full rewatch on release order starting with TOS and ending with Enterprise.

Yes