The Dreamers

Darren and Dirk Dreamer live in a comfortable two-story house. Darren, the father, is a creative sort, and would like to make a living by selling his paintings, but unfortunately, reality will likely force him to take up a more conventional trade before his items start getting repossessed. Anything is better than being unemployed, and he will have a few low-level Wants that will be fulfilled by obtaining regular employment. If you want to try and make a bit of cash on the side, you can move the easel down from the second floor downstairs or out to the curb and have him work on still lives in idle time. When the paintings are complete, sell them with the Buy menu and you should rack up a few Simoleans.

Dirk, like Dustin Broke, has the difficult combination of schoolwork and the Fortune Aspiration to deal with. You'll need to get him a job if you want to achieve any of the cash-related Wants that pop up, so try to find one with short hours that don't conflict with his trips to school.

Tips
The Dreamer house is actually well laid out, so you won't have to do any major construction. You'll find it a bit cramped when you have to entertain visitors, so as you get a bit of money, you'll want to invest in a larger dining room table and perhaps a longer couch.

The Calientes

Nina and Dina Caliente are young, independent women, living together (although they sometimes aren't very friendly towards each other) in a modern three-story building. Dina is the golddigger of the two, with her primary goal being to marry a rich Sim. When you see this Want pop up, lock it in and start working on building your relationship up with Mortimer; you'll need to get your day relationship up to 100 before you can safely propose an engagement or marriage. When you do lock your claws into old Mort, though, he'll move into your house, and bring with him around 50,000 Simoleans, which should help offset any financial troubles you've endured during your wooing.

Nina is more concerned with Romance than with making a link with any specific Sim, rich or otherwise, so you'll need to do a lot of inviting and entertaining if you want to keep knocking out Wants. She's the one that will require most of the household remodelling, as the house as-is isn't very well suited towards polyamorous activities.

Tips
You'll need to remodel the house to let Nina quickly engage in Woohoos if you wish to get her high-level Wants. It's a bit of a hike to the beds from the front door, not to mention to the hot tub on the roof, so, if it's possible, you should try to add a room to the ground floor and move the jacuzzi down to it. If you're strapped for cash, you can simply place the hot tub outside, but you'll need to use Dina as crowd control in this case. Have Dina invite Nina's many lovers into the house, then have Dina invite a single target into the hot tub for a Woohoo. This is still dangerous, though, as the AI on Dina's lovers will have them naturally gravitate towards her, so you'll probably wind up with a few catfighting episodes or slapfests.

The Pleasants

The Pleasant family is something of the prototypical nuclear family, replete with a dad that's trying to get the maid into bed, a goth and preppy daughter, and a mom that's focused solely on bringing home enough money to support everyone.

Fulfilling Daniel's romantic Wants will be difficult with the house being as full as it is. Luckily, his main obstacle in obtaining surreptitious dalliances is Mary-Sue, who's under your control, allowing you to divert her into other areas of the house while he and his various consorts retire to the master bedroom. Mary-Sue herself has the Fortune Aspiration, which is not quite as difficult to pair with Romance as the Family one is, so there shouldn't be too much friction between the two partners if you can keep her ignorant of his extramarital funtimes.

Lilith and Angela are unique in that they are the only pre-made Sims in Pleasantview with the Popularity Aspiration. This plays similarly to the Romance Aspiration, save for that you can concentrate on more general interactions, rather than having to Make Out and Woohoo all the time. Parties are also primary Wants for these crazy kids--luckily, you can throw a party anytime you want, and the Wants generally don't have to be successful to net the point reward. This means that you can use the phone to throw a party, get the points, then just ignore everyone who shows up, if you wish. Be careful that you don't have any party-related Fears when you do this, though; you can often lose more points than you gained if your party turns out poorly. (It's better to have Daniel and Mary-Sue take care of the annoying party setup aspects, such as food preparation, and let the kids socialize. Make sure you choose your party guests appropriately though, as if you invite people your Sim doesn't know, they're unlikely to actually show up.)

Tips
At the outset, the centerpiece of your house will be the large Soma television set, which offers your party guests an outstanding method of satisfying their Fun Need. You may want to consider moving it closer to the kitchen, so that party guests can shift over to it immediately after getting their initial food supplies.