When I first started playing I played mostly if not all family and knowledge sims. I have a need to have all my sims breed and I love learning, so I like making my sims learn however after awhile that got boring all the time, repetitive. I started playing challenges (that I never complete...hope to change that) and rolling a virtual dice. I've learned to like all of them to varying degrees, I need some diversity.

I've reset Strangetown and i'm not sure if i'll roll a dice or not but either way i'll add diversity. I will probably do both. The Sims that have well developed personalities i'll think about and possibly set them myself, and others if I can't figure it out i'll roll a dice and roll with the punches (pun not intended).

With that said here is how I feel personally about the different aspirations.

Family- I love. It fulfills my need for breeding and they are generally nice sims who make great parents. Knowledge- I also love as I love learning and making my sims learn and they tend to have interesting wants with supernatural creatures and wanting to get abducted. I love the aliens! Fortune- I like but eh. They feel shallow and just want more and more stuff. Fairly easy to play until I decide to make them poor, then it gets interesting lol. They do go well with family sims though. Romance I love and hate, depends on my mood. They can be fun to play and I like to make them have a baby, or more, to mess with them. Popularity I used to hate, being a loner myself it was hard to keep up all those relationships. I've learned to like them now but not my favorites by far maybe i'll learn to like them even more I think as I play them more. Pleasure I haven't played a whole lot with but they didn't seem to interesting. A lot of low level wants but I think it could be fun, with the outings and being lazy, paired with the right secondary aspiration for the sim at least. Grilled cheese is funny, I like it and it doesn't take much skill to make grilled cheese. I wouldn't want a ton of grilled cheese sims but 1 here and there is fun, maybe paired with a secondary aspiration (or as a secondary aspiration itself, i've done that too and found it nice for easy wants).

Pleasure: This one is too boring for me, and I use only when I hate those sims.
Family: I lovelovelovelovelove this aspiration, because my sims usually have 4-5 kids, and this is perfect aspiration for them, and also easy to play!
Romance: I use this aspiration when I wanna have fun, because cheating and everything else. I usually put this aspiration on vampires.
Knowledge: I use this one pretty often. I mean, I'm knowledge too(sort of).
Fortune: This one is good too, because my sims have lots of money(no cheats, just job) and usually sims who have this aspiration and a lifetime want: Earn 100.000 have a job as Natural Scientist.
Popularity: This one is boring, because I hate when my simmies have too many friends.
Grilled Cheese: Boring.

fortune, knowledge, family, romance, pleasure, popularity, grilled cheese

I used to make all my sims family and knowledge sims until that got boring without diversity then I decided to use a random number generator to decide but then I realized that I wanted aspirations to fit the sim so now I choose their aspiration/aspirations based on the sim they are and what I feel fits them best, sometimes if I can't choose between a couple i'll use a random number generator to help me decide. That being said I do like some more than others!

1. Knowledge- I love knowledge sims! So easy to keep happy by skilling, don't mind having a family or being by themselves. I haven't played much sadly with the supernaturals yet I love supernatural stuff and knowledge sims don't mind being supernaturals even wanting to be them! Though I finally found a mod to stop the "cure so and so or be cured of" wants because if I didn't want them to be a supernatural they wouldn't have become one in the first place though it's other sims that were always rolling those wants. I also love to learn myself so a sim that wants to learn, I just love it.

2. Family- Family sims love to breed and i've got to make my sims breed. I like families in the game and without babies eventually all sims would die and then what? Families keep me hopping.

3. Fortune- I find this aspiration ok. I can keep them happy in a job, they don't mind having a family, the want to skill, for their job specifically but still. If they don't have enough money for all their wants to buy something it can be difficult at times but then I may find it fun because I can be sometimes be mean to simmies lol. Sometimes a fortune sim will be mean and just want money money money and things not caring who they step on on their way to the top. Other times they can also be nice. A fortune sim can be so many different ways it can be interesting.

I'm not actually sure about the order of the rest of these.

4. Popularity- I've hated these sims but i've come to like having diversity in the game and come to like all the aspirations though to different degrees. I don't want too many popularity sims, all they want is more friends and it gets difficult to keep all those friends. But I don't mind having a few popularity sims now, as long as it fits that sim.

5. Pleasure- I've never bothered really with this aspiration but i'm not sure why now that I think of it. I used to think it'd be so boring, and difficult with their low level wants to play on the couch, bubble blower etc. I've played a little with them. Now I think it could be really fun to play! Probably not to hard to keep happy, and I could always add a secondary aspiration too.

6. Romance- I used to not like these sims at all because they wanted nothing but to woohoo with everyone. Now though I think they are fun, as long as I don't have a ton of them because then things in the neighborhood can go from a good amount of drama to utter confusing chaos. I like the drama they bring now and I like making them have a baby, or babies, even though they don't want to mwahahaha. Romance women become single mothers but so far i've always made them fall in love with their babies and be good mothers though they still kept their romance woohoo with a lot of people ways.

I've played Grilled cheese a little and I find it fun and funny. A secondary aspiration can always be put on the sim if pure Grilled cheese gets boring. Even though all they want is Grilled Cheese they don't mind being told to have a family, get skills, get a job or whatever.

Edit: I didn't realize I had answered this before

Romance- Romance sims are made a million times more fun by autonomous casual romance. If they want to have Public Woohoo, they can go to a community lot alone and find someone to do it with on the park bench and then never talk to them again.

Romance/Knowledge- My favorite combination hands down, because they're so crazy and intense. I gave Bella Goth secondary Knowledge because it explains why she would be hanging around telescopes. Right now she wants to have Woohoo with 5 different sims or get struck by lightning. Y'know, whichever comes first. Time for a romantic night in the love tub. In a thunderstorm.

Fortune/Romance- My aspiring rock star sim has this. He just attended his sister's wedding, and right now he actually wants to get married, but only if the girl is rich.

Romance/Family or vice versa- These are hilarious for the I-wanna-have-babies/oh-god-no-babies factor.

Pleasure- I always thought Pleasure was kind of a throwaway aspiration made to showcase features that were introduced with Nightlife. I still feel that way, but I do give sims this aspiration, usually when they're really Playful but deficient in other areas. They're generally pretty unhappy though, unless they just bought a car or something.

Pleasure/Grilled Cheese- this is the combination I changed Natasha Una to. I wanted to keep her, ahem, flavor, but primary Grilled Cheese isn't fun to play ever.

Pleasure/Family- I gave this to a sim who's really playful but shy. It's good for a sim who likes the simple things in life.

Knowledge/Family- I gave Stella Terrano secondary Family and I had to change her OTH to Cuisine because even with just a little enthusiasm she wanted to cook/gain cooking skillpoints allllll the time. It's actually fun for me because I have a ton of custom food and there's still meals I've never seen.

Knowledge/Fortune and vice versa- Good for work-at-home type sims, especially painters.

Knowledge/Romance- They mostly act like Knowledge sims, but they can go through wild phases. They're the most suited for the secret society because in my game it's basically an orgy + the career rewards.

Popularity- They're so cute, they just want to be everyone's friend. But sometimes they want their friends to almost die! ("Defeat the Grim Reaper") Weirdos.

Popularity/Fortune and vice versa- Powerhouse career sims.

Popularity/Romance- This normally wouldn't occur to me because Popularity sims aren't that lusty in terms of their chemistry with other aspirations or their wants. BUT I changed divorcee Opal Contrary to Popularity to get her with General Buzz Grunt and her LTW changed to Fall in Love with 20 Different People (I have a mod for any LTW). This LTW with Popularity actually works because in order for sims to fall in love they have to be best friends too.

Grow Up- I love that they want to skill like Knowledge sims. Sally Riley is shipped with the lifetime want to Max all 7 Skills, so I'm playing her as a homeschooled (Simlogical mod) child genius and I'm going to make her permaplat while she's still a kid.