I want all the tea and the drama...

I think the hardest household play goal I made myself was when the Discover University pack came out. I made a duplex and all sims on the lot were housed in one or the other side of the duplex with strategic door locking. My friend, PugLove888, made two young adult males (one for my sim to aim to marry) and female for this plan, and I also used EuphorialQueen's Reese Cheung. These four sims were my target roommates for this family (three at a time for most of the playthrough). 
My goals were:

• have a butler
• have three roommates 
• build, test, and live with a Servo bot
• have my young adult sim develop a relationship with one particular of the roommates and marry him
• have the young adult, her new hubby, and her two parents all go to University with great grades in honors programs and graduate with honors
• have all of them go to full time classes, live at home (and I think they all worked either part-time or full-time jobs at the same time)
• have the dad in the household and the new hubby of his daughter major in robotics (they also built the servo together at home)
• have the daughter and her hubby have a child... and this child was a toddler through the entirety of the toddler needs decay bug that made raising it to a reasonable level of skills and happy one of the hardest things I've done in game in-and-of itself (I never once did a 'fill needs' cheat or something like that with her, as far as I remember, though I did have to do the 'reset' one a number of times on the roommates, and maybe some on the toddler(?) when they froze up)
• test the roommates functions (the feature was brand new with the pack), how to keep them happy, how to develop relationships with them, etc., and whether it was possible to have a specific sim for the roommate (as in all three of mine were sims I added into the world)
• all of my sims always have autonomy on
• I think the dad was even abducted by aliens at least once in this playthrough, as he was a Space Ranger and that happened to him more than anyone in my game. I think I finally put one of those satellite dishes on the roof. Oy vey! 
• I think I had a dog in the household at the beginning of this progress, also, but he moved out to make way for others as the story progressed.

Never have I ever ridden the pause button and queued so heavily in my game. I learned a ton about how the college classes worked for those living at home and commuting, about roommates, & Servo... and we all made it to the other side. They all graduated with honors, the daughter fell in love with and married the roommate as intended (as I mentioned above), so he joined the household. I then added Reese as the third roommate. At one point I decided to have the other two roommates get married, so I had them join the household (maybe that's when the dog moved out?)

My plug for butlers...
...And never has one of my butlers ever so heavily earned his pay. If he wasn't repairing the Servo, he was tending the garden, picking up after everyone, cleaning, socializing with kids and pets, cooking, and just plain being busy nearly continually with a great attitude.