To record achievement popups using OBS, make sure you check the box for "Capture third-party overlays" when adding your Game Capture.
How to remove Overboard! achievements from Steam on Windows
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Launch run (WIN+R)
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Type the following and press enter: steam://open/console
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In Steam Console that opens, type in the following commands one by one (sadly no batch support seems readily available)
achievement_clear 1546920 A_GoneToPrison
achievement_clear 1546920 A_EscapedPrison
achievement_clear 1546920 A_EscapeWithin3Hours
achievement_clear 1546920 A_EscapeWithin5Hours
achievement_clear 1546920 A_MadeSomeMoney
achievement_clear 1546920 A_FullHouseIn5Hours
achievement_clear 1546920 A_FullHouseIn2Hours
achievement_clear 1546920 A_NoLooseEnds
achievement_clear 1546920 A_NoLooseEndsIn5Hours
achievement_clear 1546920 A_NoLooseEndsIn4Hours
achievement_clear 1546920 A_ReunitedWithMalcolm
achievement_clear 1546920 A_GotYourMan
achievement_clear 1546920 A_TalkedSomeoneDown
achievement_clear 1546920 A_GodCriticisedPoetry
achievement_clear 1546920 A_SteerTheShip
achievement_clear 1546920 A_Liason
achievement_clear 1546920 A_DruggedAnOldLady
achievement_clear 1546920 A_Blackmail
achievement_clear 1546920 A_WinAtCards
achievement_clear 1546920 A_AllMalcsStuffOverboard
achievement_clear 1546920 A_DoubleHomicide
achievement_clear 1546920 A_TripleHomicide
achievement_clear 1546920 A_QuadrupleHomicide
achievement_clear 1546920 A_QuintupleHomicide
achievement_clear 1546920 A_HextupleHomicide
achievement_clear 1546920 A_SeptupleHomicide