Quote from doublet83:
I will share some learnings I've had on the tax front.
For someone with substantial income and limited deductions, there isn't a clear cut option. As a disclaimer, I'm no tax professional, so my understanding can be wrong.
Treating myself as unemployed:
No self employment tax. +
Can't deduct expenses - (but not a big deal since I don't have much)
Can't contribute to IRA -
Professional Trader Status
No self employment tax +
Can deduct busineses expenses +
Can't contribute to IRA -
Must quality for trader status and may be subject to greater IRS scruity
Can not deduct certain expenses such as healthcare (?)
LLC - S Corp
Self employment tax and payroll taxes on the amount your self desginated salary -
Can deduct busineses expenses and health insurance+
Can contribute to IRA, I believe 41k annually +
More complicated returns and I believe significant reporting costs -
I've talked to two tax professionals. Generally an unpleaseant experience. I got the feeling that I was being squeezed after they heard my income, and was being overcharged and perhaps sold services I did not need. These accountants are salesmen first, and accountants second. I paid for a 30 minute consultation with Robert Green for $150, and he seemed knowledeable, although I didn't like how he liked to talk a bunch rather than directly answering questions that I wanted answered. The other tax accountant was much worse and pretended to be proficient with trader specific issues and got some things wrong that even I was able to identify.
Given that my strategy is largely focused on medium to long term investing, I decided to focus more on this tax efficient strategy in an attempt to realize more longer term capital gains: If a long position runs up to a point where I can normally inclined to sell, instead, I would consider holding and writing a moderately to deep in the money call. This sort of locks in my gains up until a certain amount as I attempt to hold the long position for long enough to benfit from favorable capital gains tax rate. I would consider this a form of tax arbitrage, as I do not believe the options are priced for this enabled tax efficiency. Certainly an imperfect strategy, and not the same as locking in your gains, but I do complement it with a view on volatility pricing based on bottom-up analysis.