Shouldn't this start with 3.5 billion years Ago: TNG All Good Things...?
An actual chronological edit of all star trek would be fun, opens with two scenes of Picard yelling at Q in the mud, jump forward to data hanging out with Mark Twain, then the Guardian of forever and Enterprise fighting Time travelers in WW2. then you have the DS9 Crew messing around in Roswell NM, then the events of the Journey Home.
Voyager was present at the big bang, also thanks to Q, so that's got to be your first scene. This would be a massive undertaking, but a lot of fun to see.
It's interesting, but I don't think viewing order has to be chronological. If someone is adamant about watching everything, I'd recommend they go by production order.
This is true for pretty much any franchise. If you're going to watch it all, you can't go wrong with release order. That way you have the same context that original viewers did, and what the writers likely had in mind.
That doesn't mean TOS the best starting point for newcomers, though, since they're probably not committed to thousands of hours of Trek right out of the gate. They're gonna bail if they don't like the first few episodes they watch.
Currently watching it in chronological order with my partner for the 1st time, just got to season 4 of ENT, shit is getting crazy in the Temporal Wars.