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I believe you have to use both of her services at the final walkthru.
Cathy 1
Envy 2
Bella 1
jade 1
Jill 1
Josy 1
Lilly 2
Maya 1
Melaine 1
quin 2
Riona 2
Sage 1
Sarah 2
these are the only ones you can buy to get the trophy
""
So one thing, I *BELIEVE* I've had something similar to watch out for...
So the "comissioned artwork paintings" (from jacob) need time to "be painted".
I ended up solving the issue for me (and get the achievement) by loading an earlier game & (re-)purchasing an image that was still buyable (even though I had all allegedly unlocked) and then fast-forwarding time until the next D**-mansion free-roam, where I got a message from Jacob stating he'd delivered more art.
So it's not just about BUYING them, but also getting them delivered by Jacob. It's *NOT* an instant "unlock", in that regard.
""