Heidi: Health. She has bad teeth, infection-prone ears, and she's quite lumpy and bumpy. Granted, she's improved 100% in the last year with good food and good veterinary care, but still. I wish she had a better baseline.
Missy: Seperation anxiety! That is by far her biggest anxiety, and the one that causes the most day to day problems. I can handle the storm/firework issues, I don't mind her being shy, and her dog issues are pretty easy to manage. But the seperation anxiety is hard on everyone.
Jack: Stranger danger. I will keep the resource guarding, but the stranger issues limit where I can take him, what I can do with him, and requires constant training and management. It makes grooming/vet stuff a VERY BIG DEAL.
I think all those things would make my life easier (and in Heidi's case, cheaper), but I think life would be easier on them without those issues, too.