For the people saying Macky isn't working... I am not sure what you guys did but you must've broke into her apartment and sniffed her shoes before doing all the other stuff (I mean really who wouldn't avoid someone who did that entirely unprompted?).
I have a note of saves so I can easily know where to get what save to load for which scenes, and I will post my notes here so you guys know how to progress with Macky. You can RNG sleeping through classes as you probably have experienced, but I never skipped by working at McHearty's until I started going for this, so I start with 0 skips and something like 10 or 11 sleeps.
You can ignore the #'s on the side, thats just the corresponding save on my game.
1 = beginning macky skips
2 = after 1st assignment done, before turn in (3 skips or 6 skips cant remember, get the assignment/talking to on a Tuesday or Thursday since you have to meet Macky on an Afternoon so you can do the assignment and turn it in during the Evening)
3 = after 2nd, before turn in (happens after another 3 skips as long as you have enough sleeps as well)
4 = after turn in and sniffed shoes once (I didn't try to sniff more here)
5 = after 3rd, before turn in (another 3 skips with enough sleeps, it should be 3 and 3 for both each time)
6 = post stage 2 sniff (again only one sniff attempt here)
7 = after 4th, before turn in
8 = sniff
9 = next assignment, before turn in, after saying id like to apologize as my dialogue choice (Another Tues/Thursday here, I also skipped another 3 but may not be necessary)
10 = after turn in, then reached 12 skips 15 sleeps
11 = after next meeting with macky (evening after class, so looks like it needs to be Monday/Wednesday/Friday), go to her next day and get assignment, study it however, before turn in and then you can ask to sniff
12 = before slept in class 2x on monday, evening you get a meeting with macky
13 = after, you can break into her room at night, right before nighttime sniff
Can't go any further right now, but this is basically to the end as far as I know. There is a scene when shes walking around at night that occur after the I do last thing I have written down, and potentially a bit more? I think something was added as part of this update.
Edit :
I actually got free time and just figured I should finish it off :
14 = after, at this point youve unlocked basically all the repeatable shoes/foot stuff. speak to macky at night while shes patrolling the school for another.
15 = after patrol scene, speak with her again and select "can i" -> "foot lick", then head to her room. this event has multiple endings. looks like 3 possible events/endings, if you ask to be her bench (first "Can i" thing) it will change what you do in her room (maybe, it seemed to do that when I tested)