This is my Status quo:
And only Chloe to train
Actually I think your game is broken as you miss things in the gallery that should be unlocked like the one on your gallery 1 photo
top row all the way to the right.
Which is penelope with the fuck machine, which you should have unlocked I guess because you have made her your slave already.
And I am not sure if you can do that without doing all her shoots in advance.
You can try to buy the fuck machine (if you havent already) and go to park and see if can you start the shoot.
But on the other hand maybe it is better for you to wait till version 1.9 drops.
With version 1.9 you need to restart the game anyway or use the savegame that is provided with the game by tinwoodman which wil have everything unlocked up to version 1.9 i guess.
And when you decide to replay it yourself, then first fail to pay rent by buying stuff (clothing) till your out of money to unlock the one on page 3 first one on the left top row.