Here's my fake Boss's Day Marathon. Mainly episodes about Dave, Jimmy or other News Directors.

Noon till Eight.

12:00 Who's the Boss? - Part 1 (Bill)
12:30 Who's the Boss? - Part 2 (Bill)
1:00 Pilot (Bill-Catherine)
1:30 Pure Evil (Bill-Catherine)
2:00 Review (Bill-Catherine)
2:30 The Crisis (Bill-Catherine)
3:00 Halloween (Bill-Catherine)
3:30 French Diplomacy (Bill)
4:00 Bitch Session (Bill-Catherine)
4:30 Rat Funeral (Bill-Catherine)
5:00 Public Domain (Bill-Catherine)
5:30 Ploy (Max)
6:00 The Secret of Management (Bill)
6:30 President (Bill-Catherine)
7:00 Retirement - Part 1 (Max)
7:30 New Hampshire - Part 2 (Max)

I chose "Ploy" because it deals with Dave having to swallow his pride to keep Max as an employee.

And "Rat Funeral" because it's about Dave as the boss trying to show his employees that he's a nice guy.

And I end the marathon with Dave losing all his employees except Matthew.

Solid lineup. It looks like you've covered everything pretty well. Kudos, by the way, for including The Secret of Management, which happens to be one of my all-time favorites.

-Dale