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Watching Order?

I think I'd go crazy swapping the DVD every episode if I wanted to watch the franchise exactly in chronological order. Personally, I'd watch it like this:

TOS 1-3
Movies 1-6
TNG 1-7
Movies 7-10
DS9 1-7
VGR 1-7
ENT 1-4
Movie 11
 
Should I jump around between TNG and DS9, DS9 and Voyager since they overlapped? Am I caring too much? Please help me with the order of things... :)

No, you should not feel any need to jump around because the serieses 'overlapped', because really, they barely overlapped at all. There is actually very little cross-series story points, and the few that are there are mostly just throwaway lines that don't amount to much. Heck, even the serieses themselves, other than DS9 (which is the only Trek show with ongoing story and character development), almost never have story points that cross from one episode of the same series to any other episode of the same series.

Yes, you are definitely caring too much because aside from DS9 , the order you watch things in is almost entirely irrelevant for the aforementioned reasons. Each episode is standalone (again, aside from DS9), and so is each series.

In other words, the makers of the shows did not put nearly so much thought into overlapping stories from series to series as you are giving them credit for. Rather, in reality, they put almost zero of that in.
 
Should I jump around between TNG and DS9, DS9 and Voyager since they overlapped? Am I caring too much? Please help me with the order of things... :)

No, you should not feel any need to jump around because the serieses 'overlapped', because really, they barely overlapped at all. There is actually very little cross-series story points, and the few that are there are mostly just throwaway lines that don't amount to much. Heck, even the serieses themselves, other than DS9 (which is the only Trek show with ongoing story and character development), almost never have story points that cross from one episode of the same series to any other episode of the same series.

Yes, you are definitely caring too much because aside from DS9 , the order you watch things in is almost entirely irrelevant for the aforementioned reasons. Each episode is standalone (again, aside from DS9), and so is each series.
That's certainly true of TOS - you can watch it in any order you want. But it's not entirely true of the other series. TNG mostly consisted of standalone episodes, but it had a couple of storyarcs (Worf and the Klingon political situation; Tasha Yar and Sela; Data and Lore; Ro Laren's introduction in S5 episode "Ensign Ro" and exit in TNG's penultimate episode; "The Best of Both Worlds" followed up by "Family") although it happened rarely and involved maybe just 15-20 episodes in the entire run of the series. I'm currently watching Voyager season 2, and while it's mostly standalone, it does have one storyarc. I haven't watched enough of ENT to comment, but I think it had some arcs, too.

It's also not quite true that series do not overlap at all. DS9 references the events of TNG on at least two occasions: the pilot "Emissary" references TNG episode "The Best of Both Worlds" that aired a few years earlier, and it's certainly advisable to watch TNG before you see season 4 of DS9, when a regular character from TNG became a regular on DS9 right after the end of TNG. You'll certainly understand the character and his story better if you are aware of his storyarc in TNG (and he was one of the few people in TNG who actually had a storyarc). Another one of DS9 regulars used to be a recurring character on TNG, but he wasn't that prominent on TNG and you don't really have to see it to understand him. But, if you just watch TNG before DS9, you'll have no problem with any of it. The only instance where the chronological order of episodes matters is the Maquis arc that GodBen mentioned.

edit: Also, DS9 season 3 episode "Defiant" features an appearance from a major TNG character and references a TNG season 6 episode in a very important way.
 
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The complete Season 3 of "Enterprise" (strictly speaking, the final episode of Season 2, the whole of Season 3 and the first three episodes of Season 4) consitutes a single arc.

Enterprise's third season is similar to the first six episodes of DS9's Season 6 and the final ten episodes of DS9's Season 7. This makes Season 3 of Enterprise the most arc-driven season of all Star Trek.

There were also a few episodes of Seasons 1 and 2 belonging to story arcs. The most extensive was the "Temporal Cold War", which was never going anywhere and was quite boring (sort like The X-Files's arcs). The "Vulcans vs. Andorians" and "Archer vs. Duras" arcs consisted of only three episodes each.

Season 4 mostly consisted of two-parters and three-parters (called "mini-arcs" by the producers) which sometimes were buildung on each other. For example, the Klingon Augment project in the Affliction/Divergence two-parter was a result of the Augment incident in the Borderland/Cold Station 12/The Augments three-parter.

All in all, Enterprise was probably the most arc-driven Trek series after Deep Space Nine (with Enterprise's Season 3 the most arc-driven season of all Trek).
 
There are certainly cross-references for the bits of TNG and DS9 that overlap (including the movies) and likewise for the later TNG movies, DS9 and Voyager. They're not that crucial, but if you are intent on watching the whole saga from beginning to end, I'd definitely recommend the chronological (stardate) order during these overlaps, as posited by people who've already posted.

Although there was overlap in terms of the production dates between the late TOS movies and early TNG, obviously there's no story overlap, so it's safe to watch ST:V and ST:VI before proceeding onwards to TNG S1.
 
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