Just finished Wonder Man a few hours ago and here are my timeline notes:
Ep4 - flashback episode from Simon’s perspective (last year incident on the rookie?) (2025?)
Ep1 - day 1 (Tuesday) not long after April 1st
Ep2 - day 2 (Wednesday)
Ep3 - day 3,4 (Thursday/Friday)
Ep5 - day 4,5 (Friday/Saturday)
Ep6 - day 5 (Saturday)
Ep7 - one week later at the least day 10/12,day 11/13, day 12/14 (a few months since before ep 1. In late March perhaps)
Ep8 - day 12/14, day 13/15 ,time jump to the premiere of wonder man, time jump to Simon breaking Trevor out about 3/4 days of shadowing.
Also for clarity I believe iron man 3 happens in December 2012 not 2013 but because Trevor would more likely be somber after he was arrested in early 2013 so early 2026 works and doesn’t really overlap with anything where as having it in 2027 just muddles up DD:BA S01 and Brave new world so I’m putting it in early 2026