Final answer:
Simon can deduct $9,850 for gambling losses if he had equivalent gambling winnings. Other expenses like investment management fees, tax preparation fees, and transportation costs are not deductible under the Tax Cuts and Jobs Act (TCJA) effective from 2018 through 2025.
Step-by-step explanation:
To calculate the amount Simon is able to deduct for his expenses, we need to consider tax laws. Typically, gambling losses can be deducted to the extent of gambling winnings, investment fees may be deductible depending on the type of investments, tax preparation fees might be deductible as miscellaneous itemized deductions (subject to 2% AGI floor), and unreimbursed employee expenses like transportation costs are also considered miscellaneous deductions.
However, under the Tax Cuts and Jobs Act (TCJA) effective from 2018 through 2025, miscellaneous itemized deductions subject to the 2% floor have been suspended. This includes investment management fees, tax preparation fees, and unreimbursed employee expenses.
Therefore, without specific information concerning Simon's gambling winnings, we cannot determine the exact amount he can deduct. If we assume he had gambling winnings of at least $9,850, he can deduct the entire $9,850 in gambling losses. The other expenses ($2,660 for the broker, $1,055 to the accountant, and $2,880 in transportation costs) would generally be nondeductible during the suspension of the miscellaneous itemized deductions under the TCJA.
In conclusion, if Simon itemizes his deductions and had sufficient gambling winnings, he would be able to deduct $9,850 for gambling losses. The other expenses listed would not be deductible under current tax law.