A Hard Lesson About Taxes And Getting It Right

I don't keep track of my trades everyday. I wait until the end of the year and run a script on my monthly statements that matches everything up (custom made software). I then check manually that my profit totals are in line with what the software is reporting based on the money I had at the beginning of the year and the money I have at the end of the year. So far this has worked well for me and I don't have to deal with the busy work of recording my trades each day into a spreadsheet.

I elected mark-to-market accounting several years ago. I just give a summary of my trades to the IRS. If they want to see all of them, they know who to contact.
 
As a side note, I wouldn't have a problem with the listing of each trade line by line for the IRS, but there is a maximum number of trades you can do this with before you cannot e-file the return. Maybe if the IRS fixed their e-filing system for unlimited trades, they would start getting more info. But to ask for a "phone book" sized return just seems ridiculous.
 
What's the big deal about not being able to e-file? Unless you are concerned about getting a refund back quickly it is a non-issue to file on paper.

As long as you're not filling the paper forms out by hand, at least :)

For the sake of brevity, I wonder if the IRS will let you aggregate your long and short term buy-sells into just two entries?
 
Quote from ElectricSavant:

keep an excel spreadsheet, not only for tax purposes, but to make sure that there trades match with their broker? I print out my sheets and put them in my file for three years. I don't care how thick they are. I have 2006 taxes...2005 taxes...2004 taxes...and 2003 taxes in one of those plastic crates from Office Depot.

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What is excel and how do I learn it or get it?
Thanks
 
Quote from Traveler:

What's the big deal about not being able to e-file? Unless you are concerned about getting a refund back quickly it is a non-issue to file on paper.
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It is an issue when I don't want to have to kill a tree in order to file my tax return. In this day and age, doesn't submitting a telephone book sized return seem borderline insane? It does to me.
 
The IRS sent me a letter for last years taxes and claimed I owed them 3 million dollars :D

I wrote a letter back, with some trade printouts that had big red circled A,B,C,D's around some summary info, that matched big red circled A,B,C,D's on my brokerage statement with an explaination.

They wrote back saying "thanks, that clearss it up". Hahahaha.

I never include full Schedule-D's. I give them a single summary line.

Including 800 pages of Schedule-D is worthless. No one at the IRS will actually spend time adding up all the numbers and checking them. Just dumb.

But ill be a little more clear about how I calculated my summary line in the future so they dont flag it.
 
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