I am concerned about the possibility of being required to pay penalties for underpayment of Federal Taxes for this year (1999) due to significant short term capital gains. Here's the situation:Last year (1998)Wages: $70k (fairly level throughout the year)Capital Gains: $20k (mostly long term)Taxes Owed: $606 (made some large end of year additional withholding payments)This year (1999)Estimated Wages: $85k (fairly level throughout the year)Short Term Capital Gains: $88k (not a very Foolish investor, but lucky nevertheless with initial investment of $60,000)Distribution of 1999 Short Term GainsApr: $10K (Long on I2 Technologies)May: $4KJul: $60K (Long on Oracle $30K (bought in mid 20s) then Oracle Calls for another $30K)Sep: $7KOct: $7KQuestions: 1) Was I suppose to pay taxes on the capital gains as they were realized. I had assumed that I could wait until the end of the year, since I could have losses that would offset the gains. 2) If I pay 105% of the taxes that I paid in 1998, then have I found a Safe Harbor?
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