I recently got back into trading this August and was not prepared for dealing with capital-gain tax issues. (Previous years' gains went to cover previous years' losses. This is year#1 making Actual gains.) I rang IRS to inquire if I needed to make an 'estimated tax payment' on my gains. She said, on a $60K gain I would owe $11K on federal taxes and another $10K as 'self-employment' because I have another w2-job. She told me to file a w4 worksheet, publication 505 and schedule SE. I've read many posts that I should trade under an entity, LLC or S-Corp. I was suggested to start a 2-person LLC to reap the benefits of write-offs such as: life insurance, health insurance, self-directed IRA, etc... That a one-person LLC could not offer cuz that would still box you in as 'self-employed'. My long-time CPA is too busy to return my calls cuz he started up a new office. Therefore I'm looking into another accounting firm, someone who knows more about trader's strategies. The following are firms I am considering, and would appreciate any input or experiences you may have had with them...or anyone else. - Trader's Accounting. They charge $500 for tax preparation ($100 for fees? and $400 for 3-hours of work, approx $140/ hour). They also charge $295 for a basic corp set-up or $1595 for a detailed corp set-up. - Green Trader Tax. They charge $150 for consultant fee. Then, $900-$1200 plus, for simple return or $1250 for individual and entity returns combined. Rate is at $250 /hour. - Edaytradertax. $350 for full return including Schedule D, and I need to provide the spreadsheet. (They were 2-weeks late in responding to my 2 emails for quotes, when their site says they would respond within a day or so. They're like a 2-3 person operation, so I don't know if this could make them tough to reach in case of future urgency.) So, one of my questions is, When does it become beneficial/necessary to start-up an entity to trade from? And if buying a house can offer much deduction in itself to not proclaim as a 'professional daytrader' to offset tax burdens? I'm open to all suggestions and ideas. Much appreciated.