Just a note that the Veep wiki is completely fan-edited, so if the timeline doesn't fit or seems too tight to work, it's probably because whoever edited it is as much in the dark about Veep's timeline as the next person. (But I get how frustrating it is to want the details of chronology on a show like Veep, which really doesn't care for accurate chronology at all – at least not in later seasons.)
The timeline mostly agrees with things I’d worked out for myself, based on where the elections in the show are (though there are one or two details that I think are slightly off – it has season one starting in the autumn which, purely going from Selina and Amy’s clothes in 1.02, doesn’t seem right to me).
It was the specific details of Selina’s career that I was really interested in, because the timeline for that has always bothered me – it still bothers me in fact, as Selina’s early career rise just seems too fast – but filling in some of those blanks was useful.
I think it’s only in season 6 that the chronology gets really jumpy. And it’s not even that there are big gaps between episodes, they’d done that before (about six weeks pass between Data and Tehran, for instance), it’s that the passage of time seems to have no impact on how the characters behave. As in, Amy and Mike are shocked by Leon’s stories in 6.09, despite knowing he’s had the diary for at least three months – Mike apparently commutes from DC for months at a time – Dan and Jane work together for a further three months between 5.08 and 5.09, which culminates in Dan’s firing, for reasons that are never explained -Selina mentions aches and pains that are probably symptoms of her heart attack in 6.02 and 6.03, but isn’t diagnosed until 6.04…and because the passage of time is so murky, we have no idea how long she’s been dangerously ill. (I should note, Veep almost managed to satirise the way women’s health concerns are treated with that storyline – heart attacks in women are known to be under-diagnosed, with doctor’s effectively ignoring women’s pain and telling them its psychosomatic (see for instance Serena Williams’ story about childbirth) – but failed to connect the dots, which was rather frustrating).
I kept complaining “Where in space-time are we?” because it’s hard to understand why characters are doing things, if you can’t keep track of cause and effect. For a neat example, it’s not terribly clear how long passes between Amy dumping Buddy, and going on her “not a date” with Dan in 6.05. Obviously some time passes, but I think our understanding of the significance of that event would change considerably if we knew it was two weeks or two months or four months… and the show makes it very, very difficult to work that out.
Though the most egregious offender is Dan and Amy talking about the Madison-Monroe dinner in 6.10, making it sound like they were there in different years, despite the fact that they are both referring to 2012. There’s no excuse for that, because it would have been an easy bit of dialogue to fix.