JG, I'm on Day 10X of the Angel's Path(Incest), and the events for day 1XX were a week late. Things did start happening thick and fast (oh stop it. :P) after that, though. I'm also trying to figure out how to ask about recruitment pay without naming the girls or having to put up a spoiler alert.
"A week late" is normal. There is no "Late" for the most part, as the day listed on each task is the FIRST POSSIBLE day it could happen, not a deadline.
Additional money will be plot-driven and "just in time" for any major purchases you need to make. FYI - if you're blowing all your cash on drinks, that's not essential to gameplay. So for 'recruitment pay' don't worry about it. ;)