I have two reasons not to use your system:

One: If you're committed to doing the action if you yourself can find a way to avoid the problems, then as you come to such solutions your instinct to flinch away will declare the list 'not done yet' and add more problems, and perhaps problems more unsolvable in style, until the list is an adequate defense against doing the thing.

One way to possibly mitigate this is to try not to think of any solutions until the list is done, and perhaps some scope restrictions on the allowable conditions. Despite this, there is another problem:

Two: The sun is too big.