I'll need a save file to test with to be sure, but all three of those items should trigger on the first turn (when status effects are checked)--however, there are extra conditions and not all of them interact as you mentioned.
When the "SECS" system is enabled (Arctic Rescue Nurse Outfit) and not on cooldown, the ass is exposed by the lower undergarment (if any), and the character's HP is at or lower than 0 or lust is at or over its max, the SECS ability will activate and add half of the max HP and reduce 33 points of lust.
When the character is wearing an item with the Auto Milking item flag (Dhaal Maid Outfit) and auto-milking is not on cooldown, the chest is exposed by the upper undergarment (if any), lust is at or over 50, the character is currently lactating, and the milk quantity is at or over 50% the max capacity, then the auto milking will activate, milk the current amount, and reduce lust by 20 to 30 points, depending on if the character is Treated or has any mil-related perks.
When the character is wearing an item with the Auto Condom item flag (SteeleTech Jungle Jumpsuit) and an auto-condom has not yet been applied, the crotch is exposed by the lower undergarment (if any), the character has a penis that is erect, an auto-condom will be applied (no lust or HP changes from what I can see).
Hopefully this helps and works as intended. If not, I'll try to look further into it.