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As a long time (and current) Traveller player/GM, who has forgotten more about the setting than I can currently remember, let me just say that once you start delving you will be hooked, especially if you are a fan of history. But as for the settings, let me give you a quick breakdown if you haven’t read about them yet (in Traveller timeline order, not published order, and these are settings, not rules versions):
T4 (traveller version 4) aka : Mileau 0: takes place during the Zira Shurka, or the First Imperium when the Villani ruled, before contact with Earth and the Solomani. Purpose of this setting was indeed to be more Fossian, and have much more to do with exploration than other editions.
Traveller (Classic, or CT): takes place during the Third Imperium, has a very 1970s sci-fi feel to it (and that’s not bad IMHO). Enemies at the walls, intrigue, most people just trying to get by, but still a glorious time where there is stability across much of the Imperium with all sorts of adventure at the fringes and brushfire wars for the PCs to take part in popping up all over the place. Includes the Fifth Frontier War. MOngoose Traveller takes place during this time, just before the FFW for the most part.
MegaTraveller (MT): Takes place in the wanning days of the 3I. Basically an assassination of the Emperor sets off a rebellion/civil war with all sorts of claimants to the throne, including someone claiming he is the REAL Emperor as the one dead was a double. Lots of destruction and infrastructure failure. Enemies invade while the Imperium is weak, Vargr take over worlds, Spinward Marches are left on their own. A very gritty time where everyone is having a hard time getting by at all, and most are sided with one faction or the other. Kind of breaks the setting IMO, though I had some good games in it.
Gurps Traveller (GT): Takes an alternate history view as in their line Emperor Stephrone is not assassinated.
Traveller New Era (TNE): One of the sides in the Civil War lets loose a computer virus sort of thing that causes spaceships and stuff to go full on sentient and start obliterating any living things. People, planets, etc… It’s basically another Long Night scenario, but with added dangers. Games set in this time period revolve around bring civilization back, exploring/reconnecting, surviving the Vampire Fleets, and the occasional smash-and-grab for rare resources and tech.
Now, I would recommend CT era as it’s well “documented” and less wiley-nilly and frenetic than the later time periods. To me the best 2 starters for the setting are The Travller Adventure (which you can find in PDF) and as mentioned above the 2 Library LBBs. These will give some background. All of the LBBs are available in PDF, and you can also order a CD from Far Future Enterprises with EVERYTHING. Board Games, the Challenge and Travellers Aid magazines, all of the supplements and adventures… everything that was done by GDW. (The 3rd party stuff by FASA and Judges Guild and such are more difficult to track). Most of it is pretty good, though some are crap scans that you can read but are crooked. Highly recommended though.
Now, you can also go to http://www.downport.com/ which is a phenominal resource, as well as Freelance Traveller. There is also a free interactive map at https://travellermap.com/?x=4.272&y=77.581&scale=7.7265625 that has info on a lot of the systems and their histories (though a lot of the info is geared for TNE, there is also usually info pertaining to CT)
A lot of the early adventures are indicative of what was going on in Cinema at the time, but to me the best for the true Traveller flavor are The Traveller Adventure, Secret of the Ancients, and a lot of the stuff Martin Dougherty wrote that was for T20 (aka Golden Age) that I think is still on RPGNow. THis is of course YMMV, as everyone has their own favorites. I really do like the history, and once spent 2 whole weeks of college winter break doing nothing but tracking down Traveller books and devouring them (pre-internet, of course!). For me, the setting is no longer Hard Sci-fi, more space-opera with hard sci-fi elements, but that’s not a bad thing to me!
"I saw this in a cartoon once, but I'm pretty sure I can do it..."