If you give someone an option, even if it seems like one you don’t want, assume the worst and act/protect yourself accordingly:
In the Rent-A-Center deal, there was actually a lot of work to do, and it distracted Vintage from the extension deadline. In the Van Halen deal, there wasn’t particularly, so Monk cleverly created a lot of work to distract them, and it (apparently) worked. One lesson here is, keep a checklist of your deadlines. Another lesson might be, just because you have a deal with someone and you are working hard together to achieve some goal, don’t just blindly assume that you are partners and your interests are aligned: Think about what the other person’s interests actually are, and keep in mind what your contract actually requires.
A third lesson might be, it is common in finance and economics to assume optimal exercise of options: If someone has the right to do something, and it is in her clear economic interest to do it, that is assumed to be equivalent to “she will do it.” That is a good enough assumption for most cases, but in the real world, sometimes people just forget.