If needing to raise Cait's affection, one can do so by exploiting a terminal that controls a safe. The player character can unlock the safe, which will boost Cait's affection, lock the safe again via the terminal, quicksave, and load. This method will bypass the "refractory period" on Cait's affection and allow them to boost her affection in a relatively short period of time. One such location is http://fallout.wikia.com/wiki/Fiddler%27s_Green_Trailer_Estateswhich is along the western edge of the map, south of Sanctuary.
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The quest might not trigger after Cait's dialogue. If that happens, you can workaround this by not allowing her to talk to you about it (choose the "Maybe Later" option).
You need her to not be your companion but you can't dismiss her directly without triggering the dialog. Find another one of your companions, and ask them to join you. Send Cait on her way. As she is leaving, talk to her.
This will trigger the dialog again and this time the quest will show up in your quest log.
To trigger Cait quest AFTER the bugged conversation, you should:
1. Get rid of any companion (you can do this by talking to them and choosing appropriate dialogue branch),
2. Stand in front of Cait,
3. Open console, ` by default, execute setstage 1666c5 0
4. You will be fast moved to a place near Vault 95 and "Benign Intervention" quest will immediately be triggered to start, so you can see it in your quest log.
5. Talk to Cait and make her to be your companion,
6. From this point you can be sure that if you follow all other advises in this section you will not encounter any bugs during the "Benign Intervention" quest.