On another note started a fresh playthrough and backing up my save each time I do a mission, had multiple breaks again but by resetting and trying again I managed to clear all quests so far to clear properly. It seems to be some kind or script trigger issue. For Example in "Paving fun with a box" you have to leave the dialog with the trader before you buy the shipment otherwise the "Find the Trader" step won't trigger. Same with "Naughty Goods Show" if you give the Tentacles to Paya directly before leaving the dialog first "talk with Paya" won't trigger