it IS possible to do this achievement and the "self-actualized" Upgrade everything in the same play through.
to get both follow the collectible guide below , DO NOT UPGRADE ANYTHING TILL NEAR THE END, with all 42 contraptions in hand, go thru the load screen to "the bridle path" (as part of the manor mission). the game auto saves during any load screen so upgrade everything for this achievement then quit to main menu, LOAD GAME from main menu DON'T start a new DLC game. you will be right before you upgraded everything and can carry on with no upgrades.
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