Hardest Math Problem Ever? Or is it?

Most mathematicians legendarily claim that the hardest math problems ever are the "Millennium Problems." In fact, if you solve one of these you are surely well off for life, financially. Yes, the prize is one million dollars, but the real money is in the fame. Everyone will recognize your work and universities everywhere will always be interested in you giving lectures - not to mention writing a book about solving it and so forth. https://en.wikipedia.org/wiki/Millennium_Prize_Problems 

However, the harder problem than that would have to be what Leibniz was renowned for attempting. His idea was to quantify EVERYTHING into math and therefore be able to calculate anything and everything by simply plugging in the values. Should I wear the White shirt today, or the Black shirt? According to Leibniz, all you would need are the values of each shirt. From there, one could simply calculate which option is the better one. The reason why this would work would be because the "values" would have all information about that variable described. Looking at the value for the shirts in said example would tell you EVERYTHING about them. The question with this though is if such values are even possible to accurately ascertain and if so, then how helpful would it be? Although it sounds theoretically possible to assign values to EVERYTHING, I don't think it would be helpful because of Bonini's Paradox. This paradox states that no model perfectly models the thing itself because the purpose of a model is to simplify, but in doing so, details are left out. Therefore, according to Bonini's logic: the only thing that accurately models the "white shirt" is the white shirt itself and the only thing that perfectly models the "black shirt" is the black shirt itself. In using the item itself, we have the utmost accuracy, but then we did not simplify - hence why it is a paradox  

In conclusion, I claim that the Millennium problems may be the toughest math problems, but Leibniz's bold plan would be much harder to solve (but I don't count it since the practical use of such a calculation would intrinsically be useless as far as efficiency goes [due to Bonini's Paradox]).