Ok, I looked into it and it seems to be very common not only for your time spent locked up before a conviction to be counted towards the sentence, but for those days to be counted as double, triple or even quadruple for time off the sentence. These pre-sentencing lockup days are called custody credits.
So to me, A&tW is coming up on the 2 year anniversary of Civil War. Or if you wanted to make it even earlier 2018, one could assume Scott's time on The Raft got him a couple weeks knocked off his 2 years.
Eh, I mean Scott was locked up for only 3-4 days, so at most liberal estimate that's around 2 weeks off.
But there's no evidence that's the case (him getting time served). Not saying it isn't, but the evidence we have indicates 2 years, and conclusion based on that is Ant-Man & the Wasp probably occurs sometime around mid-April, 2018, with Avengers - Infinity War likely occurring in early May, 2018, and the A&tW mid credit scene obviously aligning with Thanos' snap toward end of Infinity War. IW is obviously occurring during spring time based on those outdoor NY scenes showing warm weather and trees in full bloom at park, and Peter is still in school so we can assume it's before late May or early June, whenever kids in NY public/magnet schools tend to finish the school year...?
To go on a Spider-Man related tangent, we know Spider-Man - Far From Home picks up right after Avengers 4 ends. We've also heard rumors Avengers 4 picks up years later and involves time travel, so if S-M:FfH does pick up right after, and occurs during summer vacation, that would align with the theory Avengers 4 features time travel to the past to obtain the stones and prevent Thanos from getting them or attacking him directly with them. That would likely align he film's ending probably in 2018, soon after the events of Infinity War, with S-M:FfH picking up immediately after and running into summer where he travels to Europe. So Civil War set in April, 2016 was toward end of his freshman year, right (2015-2016)? Am I remembering correctly? And then Homecoming in October, 2016 is beginning of his sophomore year (2016-2017), his appearance in Infinity War is toward end of his Junior year (2017-2018), Spider-Man: Far from Home will occur in summer between Junior and Senior Year (Summer 2018), and the third Spidey film will likely be set in his senior year (2018-2019) at some unknown point in year. Interestingly to pull that off it would have to be set at least 2-3 years in past depending on when the third film actually comes out (probably 2021) unless they just throw the timeline thing out the window like Homecoming did with the 8 years later tag (it was four years and change, n00bz)
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Anyway, back to AoS/IW/A&tW placements, we can possibly assume that snow in that AoS episode (someone please remind me which one that was) was later in the year, a late in the year snow storm in late April or something. I forget the location it was set in but if it's up north it's possible. That could help push those later Season 5 AoS episodes to late April-May to align with Infinity War, using Yo-yo's recuperation time and getting arm to work could conceivably have taken a few months.
That seems best approach to take, but I may be overlooking or foregetting something so definitely let me know.