I don't know if it does or not, CC, or at least I don't remember it doing so outside of giving you a path choice. Regardless, always check the logbook first thing in the morning, and try to plan the day accordingly. Bear in mind that the events don't always occur on the days specified, especially if you still have tasks to perform. Actually, two of the meetings my character was supposed to have happened out of sequence.
"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. ;)