@DarkElmo
I’m going to be blunt with you (hopefully my comments on working girls don't offend you) and offer an alternative approach.
Let me teach you the way of the Sith (GripMaster). As I have said before these women are damaged goods and often have a plethora of issues (psychological, mental, emotional, fiscal, etc.) that they continue to make worse instead of better (pimps, bad choices in men, not saving, having an exit plan), meaning they are also dumb. I know there are exceptions to the rule but if they were intelligent they wouldn’t be here.
But you can use this to your advantage in order to amplify your experience within the boundaries of the booking. Some very solid advice - being nice is a good start but as you said don't be “Mr Nice Guy”.
If they open up immediately without prying I do like to press just a little. For example an abusive boyfriend - “god that must piss you off”, “I’m sure you must do a lot for him and he couldn’t even do that?” - something along those lines but altered to the situation. At the same maybe start playing with their legs, maybe their hair, keep the conversation flowing for a minute then when you get to a pause hit them with “well fuck em - you’re the better person”. Then immediately land a kiss and get it on. This way you sort of pick up their spirits and get their confidence up. However, do not ever mention anything along the lines of “we’ll let's get back at him” - implying that you and her need to prove something - this is a high risk high reward strategy - you could end up with a sex demon ready to unleash or all her pent up frustration out on your cock or be seen as a creep. Just not worth it.
Daddy issues - well that's my speciality but I’d like to think alongside Banana I’m SL’s in-house therapist. This is a bit more tricky and probably involves a bit more conversation but I always find the 10-15 minutes of investment here can lead to something major pornography studios would be jealous of. Send me a message about the girl at LF - I’ll be happy to help her out.
Again, it's all about reading the situation. For example Camilla and Adrianna at the Dollhouse, great providers (not my cup of tea) but they just get it on so no need for any of the above.
I just also want to comment on your earlier post about Villains in this game. Are we the villains - SF seem to think so, or is it Agent47 their new overlord? An actual pimp. Do we prey on these girls - not really - who puts these girls who clearly have issues into these positions? Would they encourage their own family members to pursue this path? Food for thought.