Here is my struggle

I would like to change the color of a reservation depending on two custom attributes (check boxes).
I see two ways of doing this:
Option 1:
Check box 1 -> reservation color ORANGE
Check box 2 -> reservation color GREEN
Check box 2 is disabled until check box one is checked
Option 2:
Check box 1 doesn't change the color of the reservation but if check box 1 and 2 are checked the reservation color turns green.
I've no idea so far which option is the best and even if one of them is possible.
Thank you very much for your help.
Arnaud