“When the stock goes bad, I clearly have a $10 1244 loss and a $499,990 non-business bad debt.”---->As long as the requirements of Sec 1244 stock are met, ordinary loss treatment for losses on a sale or exchange of 1244 stock is permitted if the loss would otherwise be treated as a capital loss. The amount of ordinary loss that an individual taxpayer may realize by reason of the small business stock provision is subject to certain limitations. Any amount of Sec1244 loss in excess of this limitation is treated as a capital loss; ALSO Whenyou, as a shareholder, loans money to a corporation, there is a clear expectation that the loan will be repaid. If the loan becomes worthless, deductibility of the loss for tax purposes is based on whether a bona fide debt existed, since advances that are not bona fide loans are generally characterized as capital contributions, andthe loan is classified as a business or nonbusiness debt. Business bad debts that are completely or partially worthless are deductible as ordinary losses, while nonbusiness bad debts are short-term capital losses only when entirely worthless.
“What if i had a smart tax adviser? What would he advise? “---> I guess it depends on each accountant.
“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?"---->As said above.