I have been using Turbo Tax Home Business. I have been importing my trades from Fidelity Investments into Turbo Tax. This has worked well for me the last few years.
Also, in the first quarter, when things were going well, I did pay some estimated taxes of about 20K. I was estimating about 40% taxes on gains at that point and divided it by 4. I was estimating my income bracket at that point. After the trading miscalculation, I stopped paying the estimated taxes.
The play on the VIAC stock was it was down 55% from its high with a 9 p/e ratio at the time. So, I expected a value bounce which did not materialize. The stock moved sideways slightly down. Thus, the calls deteriorated to expiration creating the loss. Memo to self: don't bet the bank on option statistics games and beware of too much institutional ownership in a stock. Lesson learned. The strategy works until it does not.
Thanks again all for the tax information. Sounds good. I'm just going to embrace the suck and move forward on this. Looks like I'll get that 3K deduction for life. 🙂
