Keep up with the game’s new updates, but finish up a character before you download the next update. The latest update to the game introduces the casino, where you can go to gamble. Blackjack is the first game to show up, with more games doubtlessly showing up eventually. To be victorious in blackjack, your best bet is to hit if you’re under 16 on the first two cards, and stay if you’re over 16. Your dealer will often bust, and you’ll often win if you play right.
You can get a gambling addiction which can severely goof up your relationships, your job, and more, but you can also earn a ton of money with a combination of luck and skill, and you won’t even have to advance years in order to do it, so theoretically you can earn unlimited amounts of money. Put your gambling winnings into real estate to watch the value increase over time, just like with your job earnings.
Not only can you have kids, but after the latest update, you can now have grandkids. All that you have to do is get with someone (married or long-term partner) and have kids, and the more kids that you have, and the longer that you live, the more likely it is that you will have grandkids. If you live long enough, you might even see your grandkids have kids, giving you great grandkids.
Make sure to keep spending time with your kids the whole way through. If you neglect time with your kids and you forget to check the status of your relationship, you could forget about the relationship with a kid and the relationship rating could fall to zero. If you do end up stuck in a dead relationship with a kid, check back with their relationship rating every year, and (if applicable) spend time with their kid (your grandkid) once per year.
Now, you have ribbons that you can earn at the end of every life that you live in the game. Once your character dies, they will be assigned one ribbon – for example, a lot of money earns the “rich” ribbon. Also, your character can now date as a teen, not just as an adult, so if you find someone that you’ll make a great match with, take the advantage and date them asap.
Right now, jobs and gambling are the only way to make money in the game. If this doesn’t sound like the ideal to you, then keep waiting for future updates. Look for one that relates to the various jobs, and download so that you can unlock the next segment of your jobs.