I'm still here too, I just found this thread again. So I'll be posting updates again. :)
Update: Jack is doing great in the medical career, he's already to lvl 5 or 6. As for Jill she's been too busy with the kids to do much with the cooking career. She just had her 2nd child a baby boy named Travis. So now Jack and Jill have 2 kids (Nicholas and Travis) and Jack wants to have another kid. I just recently re-installed ambitions since i haven't played it in over a year and am really enjoying it. Since it's been so long since i've played with ambitions, it's like I'm playing it for the first time. I forgot about doing extra things in the medical career while working. I thought that it was an opportunity for Jack so I didn't have him go to the medical meeting and so he didn't get as much job experience as he probably could of. I was surprised when the medical meeting option disappeared after he got off work. :lol: Jill is already looking for Mrs. Right for her son Nicholas even though he's a toddler still. While dinning out at the bistro, Jill ran into Lisa Bunch and began trying to befriend Lisa to set her up with her son Nicholas. I've also remodeled the Johnson's house a little bit since they can't afford to move and they can't really add onto their current house. It's amazing what removing a wall and closing off the living room will do for a floor plan of a house. Now they have a larger kitchen, a bigger living room, and a nursery that can fit two cribs instead of only one. :) Jack's LTW is to get to the top of the medical career and Jill wants to get to the top of the culinary career. As for Nicholas he's probably become an inventor and I don't know about Travis yet. Will Jack get to the top of his career, will Jill get to the top of her career, and will Jill really find Mrs. Right for her son Nicholas? Stay tuned for the next update, where some or none of your questions will be answered. :D