I've heard some people on YouTube say that legacy challenges get too easy as your family funds grow, but I haven't found that to be true. Maybe in the really late generations? Either way, how do you guys make your legacies or just long-play families more interesting?

home > My first-generation sims managed to build a medium sized house on the gigantic 60x60 legacy lot, and now that the second generation is hitting their teens, they're going to demolish the gorgeous little family home to replace it with a mega-mansion empty shell. (In previous legacies, I've kept the little home on the lot and later used it as a mother-in-law suite.) They'll be living in a remodel for the next few generations. Sure, they might have all of their needs met via objects, but they're gonna be probably all living in one bedroom together. No paint on the walls. One tiny light over their heads. It's kind of like starting over again, but not. They might have money, but they have no privacy! Definitely not something my party sims will be proud of.

sim quantity > This is also probably the most amount of sims I've played at once. There's the main couple, their three kids and the imaginary friend turned real, and a cat. Now the wife is pregnant with their fourth, so that'll be an 8 sim household if you're counting pets. I normally only stick with two to three!

losing all of their wealth > I think in the future, I might have one of my sim's descendants lose all of their family's money, either through gambling or perhaps stealing it all and running away to another town.

supernaturals > I originally had human sims to start with, but now the founder and her husband have turned into vampires. I think it's really fun to try to turn the entire family into other supernaturals within the game, rather than create-a-sim. The dad is currently working on his alchemy skill to turn the son into a werewolf and the younger daughter is trying to complete an opprotunity she got to turn into a fairy. (Just my luck, no sunstones are spawning!) The older daughter managed to get a hold of a elixr to turn into a witch, and she leveled up her chemistry to make her imaginary friend into a real boy. I'm considering making one of them learn how to build simbots, and possibly find a way to add a genie in too.

lifetime wishes > I really want to try to complete every lifetime wish too. There's some I've always wanted to try but haven't because it seems like a lot of work, lol.

bad traits > I'm considering making a sim with the worst possible traits try to climb up the social ladder to the top of the business or political careers. Unlucky, shy, technophobe, etc.

My family is over 30 generations and would be probably double that if I had not spent time in 4 and tons in CAW and lot building, and just in RL things.

I have an excel, gigantic one, where I have tracked every lifetime wish, every trait, every thing to do pretty much, every thing to collect, and so on, I track my family like crazy!

I run 2 parallel lines with normally one kid only for each. If ever have had a couple with 2 I pick who I want to keep and move the other out. I pick a new LTW to try for each generation. I concentrate most on one or 2 Sims to try to get that done. Sometimes they make it and sometimes no.

I have not played my family in a while and just refound them and are putting them in a new world I am doing. It is fun to get acquainted with them again.

Also, I have had my family live in many worlds. Each time EA released a new one they usually moved there. And they have lived in many of the worlds I have done. So that mixes things up a bit. They get the best lot in town and I am jealous of the homes they have had.

I have a family tree and I take a photo of each Sim to place in sheet I have. It is very fun to watch the genetics when I have put some of the photos side by side over several generations.

I am on my second go down the alphabet for names. My avatar here is Harmonia of the first round, the only evil child born into the game as of then. She was a terror and became a criminal mastermind I think it is called as an adult. She was a real kick to play!

The main reason why I was never interested in playing many generations, is because they end up gathering too much money along the way. At least the sims that don't move out of the original lot anyway. Sims gameplay lacks bad tidings.

I wish these games had 'disasters' that you could enable. Kind of how with city sim games you can enable natural disasters, the sims series could have recessions, financial theft, bad investments, gambler traits etc. Oh now I wonder if there are mods for this.

I know that many simmers would not want to go this far , but without 'difficult times' gameplay, there is no challenge I find. I find that the setting a goal at the start of a new family is the only challenge. But I usually complete that within the first generation. Sometimes a second generation , when a kid can get a head start because the family already has money.

Ofc I can roleplay bad luck and just make something up and use a cheat to make some money disappear, but that is still cheating

My generational play usually ends up in creating new families and slowly replacing all townies with descendants from old played families that way. It is nice to find out how they end up from time to time. I like to see the original family develop and build up their lot until they reach their goal and are well established. But then I hop to a new family. This all happens over generations, but I don't stay playing with the same household. This also lets me start a completely new theme for that new family, which usually reflects in a very different looking lot.

I have multiple mods to make earning money difficult. Higher tax rates, higher child support courtesy of the NRAAS SP money module, gym isn't free, gas prices for the car, taxi and subway isn't free, clothes are not free, higher grocery prices, higher bills, and no collecting. The mod that requires interviews also takes time for sims to land their dream job and I have a mod that makes advancement harder. With my last legacy, the fortune got lost to a late marriage that wasn't the planned heir. And all descendants move out and get a percentage of the whole.
While there's a steady increase, it's rarely excessive.

For me there has been more than enough to do in the game without caring how much money my family has now. And doing things with one family and excel lets me keep track of what I/they have and have not done yet. Reaching the top of every career, exploring every tomb, marry someone from each WA location, collecting every one of an item, whatever, really is not tied to what funds the family has.

Yeah, I can see how that is enjoyable. I enjoy all content as well, but I prefer to go about it by hopping from family to family. The one thing I like the most, is building up a family and their lot from scratch. These can be complete new sims, but can also be a kid from a former played family that moves out. But each household will have a different theme. Where one is a family that is all about sports (both practicing and enjoy watching), the next is some historian that robs..ehm explores tombs. Or some artists etc.

I create a caste for my own created sims to make sure they don't move and marry on their own (and some other stuff sometimes). This way I have more control over how my current unplayed families evolve. Slowly over time, the whole neighbourhood will be filled with my own created sims and their (grand)kids, each with their own story. So, I guess I do play generations, but multiple families at once. But overall, less generations I think.

It is also fun to create two or three castes, and play them as if they are rival clans. Slowly taking over the neighbourhood.

I started my family with the tiny house built room by room, and then they became more prosperous over time. I love for them to have the best lot in the world and a house I love. I live vicariously through them. It is pretty pathetic to be jealous of pixels! LOL :D

I find there are things you can't buy without Simoleans. So once your sims aren't simply trying to get by and satisfy basic needs or build up there house, I find this is a good time to get really in depth on certain skills or areas of the game you haven't explored. I actually keep the family to only one or two kid so you don't burn away a whole sims life raising kids. Sometimes I like to challenge myself with a big family, but while I like family play raising kids turns into just raising kids and it's easier to actually play the game for other reasons then raising kids if you have a teen or teen/child and their adult parents who still have time before becoming elders. Babies and Toddlers need a lot of attention, as much as I love playing them. I find this true for both my Sims 3 and Sims 2 gameplay. I never bothered with badges in Sims 2 for example and now I'm playing with it. I think it's interesting to even go back and look at old reviews of packs and see if there are things in a pack that have been mentioned in a review that you've never played with. Both Sims 2 and 3 have such massive packs I think I could spend the rest of my life discovering new game play in them.