Karmel, welcome to the Forum!
My Advice is pretty simple. Get help, don't leave it all for your Founder to do. What I did was have my Founder supermax Cooking, which is also needed for Ambrosia, two birds with one stone, as they say. She got the fridge from the Culinary Career, which helped a lot with keeping Perfect foods. Cooking is so easy to Supermax, cheeseplates count for the Menu Challenges.
Charisma in my opinion should be a free for all, take a class as early as you can, then whenever you socialise the Skill raises.
In my Dynasty I had three Sims move in with my Founder. My Founder married Hank Goddard, he was there for Photography, Sculpting and Gardening. Agnes moved in, she brought her Car and money, $100,000 straight away. With the Painting as a backup already done with Level 7 she went on to Sculpting and achieved the 25 Ice Sculptures. Chris Steel married Agnes, he did Painting and fishing. My Founder managed to get her stuff all done early on, with the money made from Consigning and her Career things were going well, she bought her Workplace, then the Park across the road. The Gen 2 Heir married the child of Agnes and Chris, they were the Artists. They have both maxed out Painting, Photography and Sculpting. Gen 2 supermaxed Painting, reached the top of the Painting Career because all of their paintings as children were kept until they were adults and then sold, with his Wifes experience at selling her parents stuff and the Suavve Seller trait it scored some riches.
So long story short, it is harder if you give your Founder more to do, I shared out the tasks and it went great, my Generation 4 is now a Child, his Mother has supermaxed Martial Arts and needs her Career, Opps and Friends, she is still a YA. Also pick the easier skills to do first, don't go for something hard like Logic as a founder/gen 2 supermax, wait until there are funds around and Moodlet Managers, Spa Treatments, Etc.
Oh and if you have LN and you get high level celebs just watch the gifts pour in. I sell them if they are duplicates, I raked in $200,000 once from selling them.
If you want to know more about what I did I have a story written about my Dynasty, as do a lot of us. Reading the stories can help you see how others did things and the order. Mine is the Jade Dynasty which is linked in my Sig. There are several that have been completed though so check those out as well.
Hope this helps and you can get a Dynasty going!