For a single parent Sim, the Nanny is a MUST, if you don't use the money cheat. Just call services, select Nanny and ask for the Track Schedule and she'll show up for your Sim's work times.
If you get NL, use the Matchmaker to find the perfect mate for that Family Sim.
And the Pleasure Aspiration is all about fun. Pleasure Sims love to bowl, blow bubbles, work the DJ booth, go out on a date, play a computer game, etc. They just love to have fun. They're fairly easy to please.
I'm having a ball with the Grilled Cheese Aspiration. One of my Legacy Sims has that aspiration and I just had her complete her lifetime want of eating 200 sandwiches, which she accomplished in her Junior Year at University. As soon as she reached it, I had her work out for a whole day to get in shape, since she got so tubby. I want the All Aspiration Platinum Graves Bonus.
I was also wary of custom content, but I have found some great clothes, hair and objects on many sites. modthesims2.com is great. I also like
http://www.parsimonious.org/.
Happy Simming!