I've been wondering these same issues. On the lawyer, somehow I managed to find out where she lives. Went there at 22:00 when a party was going on. She told me to bring alcohol in order to enter. I know that alcohol can be bought at a bar and I've yet to unlock that place since it's hidden along Jill's route.
The photoshoot. Going there with Lisa, she will only do bikini poses. I've gone a lot of times to visit the photographer and talk about her interests, but that's hasn't made a difference. Is there another pressure plate somewhere that needs to be pushed? I tried searching this thread for an answer but didn't find it.
Afaik, the lawyer arc for the office scene currently only stops till she gives MC blowjobs. However, further sexual content can be done if you visit her unit during non-party days (So no Wednesdays and Saturdays) and she'll invite MC in provided you've dropped her professionalism alot. Offer her high alcoholic content drinks (Liquor or Whiskey would do) and she'll invite MC in for 1-to-1 drink. Keep repeating the process and more and more stuff will happen eventually leading to pure raw sex.
For more risque photoshoot with Lisa/Mother Superior, you'll have to talk to the boss of Xshop and at least get her to do a promotional photoshoot for Xshop once. Then you can push Lisa for more and more stuff as time goes along for each photoshoot.
I know that alcohol can be bought at a bar and I've yet to unlock that place since it's hidden along Jill's route.
To go back to your question, to unlock Jill's workplace, visit Downtown at 1900 and you'll find her good friend Mia there. Then after a brief chat, the bar would be unlocked later on for you to visit to court Mia and also buy alcohol from Jill at the bar. You don't really have to go to the bar every time to buy alcohol after the bar is unlocked either. Just talk to Jill every time you see her at the motel, go to request and choose liquor. Once you pick your option, she'll comment that she'll bring it to you the next time. Skip time and talk to her again if you find her and she'll hand you the alcohol that you asked for
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Asking at the pub would be direct, not asking at the pub requires time skip but can be asked for any time of the day, not only during Jill's working days).