"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. ;)