Answer:
Casey would prefer option 1; that he pays the premiums ($8,000). Even if Casey cannot deduct his insurance premiums as medical expenses, his income will only be reduced by $8,000. If he decided to take option 2, his income would be reduced by $8,800 (= $10,000 - 12%), so he is saving $800 by taking option 1.
On the other hand, Jean would prefer option 2; that her salary is reduced by $10,000 and her employer pays the premiums. By choosing option 2, Jean is going to lose $6,500 (= $10,000 - 35%). If she chose option 1, her income would be reduced by $8,000, so she is saving $1,500 by choosing option 2.