According to the IRS, you can't.
You can do anything you want.
The questions is (beyond ethical questions), will it trigger an audit? And, if it does, can you defend yourself?
If in the end, the net matches the individual transactions, is the IRS really going to hit you up? For what? I suspect (and hope) they have bigger fish to fry than someone who didn't dot the I's, but did make sure that the I's all added up correctly - and can prove it.
Not saying IRS would approve this but I have heard some (or at least one) of my fellow volunteer tax-aide folks say that if somebody like you came in w/ a zillion trades w/ broker supplied documents that showed short-term and long term trades separated out and summed up w/ accurate gains/losses for each trade, he would just enter one line item on Sch D for short-term and one for long-term w/ the broker's name in place of the #shares/stock name, VAR for the dates (for various), and the aggregate gain/loss.
Agreed. see above. It's not technically correct, but if you can back it up, what's the real issue?
You can enter "various", and most software will let you do that also.
The key is to make it easy for the IRS computers to match your Schedule D numbers to your brokerage 1099s. If they match up then there's a 99% chance a human being will never look at your return. If there's a math error then you will get a query letter. (Or, ahem, so I've been told.) If there's a difference in the subtotals (even if the numbers add up correctly at the end) then you might still get a query letter.
That makes sense to me, but OTOH, I really wonder. For example, I do some option transactions and guess what? My broker does not report these to the IRS (they are not required to - don't ask me why). So, when I
do the right thing and report my option transactions, I end up making my data miss-match the reported data. That should trigger the flag you mention, yet, this has never been questioned. Have I considered not reporting my option gains? I'll leave that up to the reader to decide.
Be very meticulous about wash sales. Most brokerage statements indicate them but if wash sales end up on Schedule D then again you will get a query letter and you'll possibly end up paying more taxes plus penalties. The best way to avoid the wash-sale trap is to enter each & every set of dates for every sale/purchase so that the software can check you. Otherwise it's up to your keen eye and the brokerage's recordkeeping.
Again, this *is* an area where I got fed up with the meticulous book keeping requirements, and have occasionally reported the net of a series of transactions where a wash occurred, rather than all the carry-forward wash sale losses that are technically required. I have only done this when the wash sale was netted out in the
same tax year - I didn't want to mess with trying to carry this forward into a new tax year, that could get messy, and could violate the intention of the law, which I did not want to do. But I was younger and more naive then, and had not learned so much from our heads of State.
Again, if I did get audited, I could go through the transactions with the auditor, and we would come up with the exact same numbers. What is he/she going to do at that point, make me write on the blackboard 100x that I will enter every transaction? Hopefully, they go looking for a real tax cheat (
pssssst, try Wash DC).
In fact, this is why I like to be super-conservative on some point on my taxes. For example, I take super-conservative estimates on my used clothing donations. If I were to get audited, and everything netted out to zero, I would then start asking about amending my return, saying that this review made me realize that I had "miss-underestimated" some of my deductions. I think they would get bored with the game very quickly. I suppose they have a $ recovered goal in their review?
My father ran his own business, and that happened to him. Got audited, and the govt ended up owing him money! Unfortunatley, that made him a bit over-confident, and when the *same* auditor was assigned to his case 20 years later (!), he got caught with some minor indiscretions.
-ERD50