Conditional means depending on something else, as in "it depends". It might be one way or it might be another, you have to be flexible to be ready for either way. Contextual means relating to the broader environment. So "our plans generally have to be conditional and contextual" could be instead "our plans generally have to be adaptable (or flexible), taking the circumstances into consideration."

I would call it a "log." At a library it might be called a "check-out log."