The game has very clear choices leading to Dark/Good Paths.
Also, tasks do start on the day specified in the journal but might not trigger if there are uncompleted tasks prior to said day.
"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. ;)