tax questions

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In my estimation, the SE Tax will hurt me more than missing out on any extra deductions. It seems to me that filing as a pro is only more beneficial if I have made well over $100,000 and/or I can claim a ton of deductions. Does this sound right?

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Sounds about right. Of course you deduct half the SE tax you pay, so it is not that bad a hit. I think the break even point starts happening at around 80k of income. Again, get a CPA. You probably have deductions you are not even thinking about like the cost of your computer, etc.