I'm more puzzled about why this strategy didn't occur to Monty Brewster. Recall the terms:
Brewster suddenly finds that his recently deceased long-lost great-uncle was an eccentric multi-millionaire who was also his only living relative, and includes him in his will. Under the terms of the will, Brewster is challenged to spend $30 million within 30 days in order to inherit $300 million. There are some important conditions attached: at the end of the 30 days, he may not own any assets that are not already his, and he must get value for the services of anyone he hires. Furthermore, he may donate only 5% to charity and lose another 5% by gambling, and he may not waste the money by buying expensive goods and then destroying them or giving them away. Finally, he is not allowed to tell anyone about the nature of this challenge.Not own any assets at the end of the spending? Check.
Must get value for service? Who's to say he didn't! Check.
Not charity and not gambling? Check.
Not buying and destroying expensive goods? Check.
Just claim to have very bizarre, hard to satisfy, and consequently expensive, tastes. If the terms of the will said you can't do anything illegal, hire the Concord to take you someplace it's legal.
On the other hand, getting the "None of the Above" election result was probably pretty satisfying too....