When bartending, the 'social' status, the little text bubble icon, effectively makes your shift time drain at half the normal rate (or rather, the chuds lose interest twice as fast on any turn in which you don't keep the social icon up, whether by small talk or card tricks or flirting). Any time that icon is not lit up you want to do
something to reactivate it, or you're effectively losing turns.
The heart icon means the chuds are horny. You turn it on by flirting, turn it off by using the squirt bottle, and I think that after a single round in which you're topless it goes on automatically; not sure if there are other conditions. It means that the intelligent conversation action (which would recover three turns worth of shift time if they weren't so horny) no longer works, but adds a chance every turn for chuds to jerk off (adding to Cat's arousal, and potentially leading to either a 'tip' for you to drink or an orgasm which will add a lot to your remaining shift time). So if you haven't started working topless yet, I recommend not flirting until after you've done three turns of normal activity, then done the Intelligent conversation, then flirt immediately after that. If you're topless, don't bother trying to say anything meaningful (they won't listen) and just make the customers as horny as possible.
I think that training progress/availability is linked to a hidden corruption stat, but since it's invisible I'm not 100% sure which actions advance it at each stage. I just know that the cheat chicken warns against adding more than five points at a time, because it might cause events to play out of order. My guess each story stage will require ~5 reps of whatever is the most extreme thing you're currently allowed to do, plus any secondary narrative requirements. Which does feel slightly more natural than watching a meter go up with every interaction, but there are times when I don't know if I got the same result four times in a row because I'm actually not making progress or because the change will come on the fifth interaction.
It does seem weird that we aren't allowed to know what each drink sells for. As a general rule if you aren't screwing up too much you're always going to be making a little bit more money than your expenses take up and thus making slow progress through the upgrade tree, and higher rank drinks make more profit for the same actions than lower rank ones, but you can't really plan things down to exact margins and numbers. Maybe it's supposed to represent how Catherine is good at customer service but terrible at actual business, so you gotta let your accounting bot handle all of that?
The window licking scene is locked behind the same level of training that allows topless bartending (and letting the chuds grope you). After your first topless shift at the counter, the cyborgs will get annoyed about being treated worse than the chuds, and you start doing waitressing topless too. Per your instructions to IO, if you have your top on the 'no touching' rule is strictly enforced, but if you're topless he only takes action if you ask for help or are in immediate physical danger; the cyborgs take advantage of this much more quickly than the chuds do if you're progressing both at the same time because they're bolder and more aggressive in general, so they'll put their dicks in your hands while the chuds still haven't realized they can go any further than occasionally touching your butt.