let's say i invest in a corporation and pay $10 for the qualifying stock and give it a loan of $499,990.

let's say i invest in a corporation and pay $10 for the qualifying stock and give it a loan of $499,990. When the stock goes bad, I clearly have a $10 1244 loss and a $499,990 non-business bad debt. What if i had a smart tax adviser? What would he advise?Could i buy additional shares of stock (about $99,990 worth or so) and then utilize my $100,000 worthless stock deduction as an ordinary loss?