Why not use TXF Creator 1.3.2 (See http://www.txf-express.com)? It has direct support for Interactive Brokers. You can easily generate Schedule D. Most important, it is a lot cheaper than tradelog and gainskeeper.
This site, http://www.investotek.com, has a set of Excel macros that can consolidate day trades, match buy and sell (no wash sell calculations though), and export file to txf. Import this to Turbotax.
I used TradeAccountant for my 2007 return for Form 4797 and it was fine. However I had to spend a couple of hours a day for about a week to sort out the order of my approximately 1500 transactions. I decided to check out Tradematcher and within a day I got the completed Form 4797 and the worksheet with all my transactions. The owner, Wayne, was very helpful and his service was fast and very inexpensive. Highly recommended. Thanks for the referral spup345
According to their product manager Steve Boyle on 3/27/2009, you cannot export your trade transactions from Gainskeeper. So if you want to leave, good luck. Can you imagine if a broker or Quicken did this?
I have used TradeMax for a long time, really easy-to-use and possess powerful funciton which can solve all of the problems you mentioned. Wish you good luck!
IB's Schedule D Worksheet has worked for me for several years now. Mine runs about 60 pages, and I send it to Kinko's for 2-sided printing. A few years ago, the IRS put out a "clarification" stating that they expect taxpayers to send details of all securities trades with the filing, and that it was not satisfactory to simply provide it upon request. But down near the bottom of the document, it also said that, if the taxpayer files on time and pays the required amount of tax, the IRS will not usually seek to impose a penalty. My policy is to give the IRS what it wants, especially the easy stuff, in the hope (in vain, maybe) that they will leave me alone. Sending the details is no problem for me, now that IB provide a good document. Nowhere in the IRS clarification did it say that the detail has to be printed on paper. If my worksheet were a few thousand pages, I would burn it onto a CD and send that.
I bought some ASX and TSX stock. When I import IB's data into Quicken, IB feeds AUD or CAD amount. This really mess up my data in Quicken. I have tried TradeMax. TradeMax converts IB's AUD and CAD data into USD automatically, and it uses download-able daily exchange rate.
Just finished processing 30,000 matching transactions via Wayne @ tradematcher.com (trying to get a headstart on filing this year again). His prices went up this year, which is understandable given that I had no clue how he could afford to spend all that time processing these things for folks for such a low price. It's still a very fair price ($99.95) relative to the time he saves (me) and the cost of standalone software out there. So another thumbs up for him. I found it easiest to download my IB monthly's in tradelog format (it goes to many decimal places for highest probability of matching the 1099 sales number) and then using that as the input. I may tinker with excel macro's myself next year and see if I can do it myself in the future, we shall see...I can't imagine it's super hard to match the trades via excel, but who knows. As for some of the previous posters about sending in the sch. D, my accountant does the same as someone said, which is to send in the "bottom line" numbers and he keeps the (in my case) thousands and thousands of pages of pdf files locally, available if ever needed (which he said has been maybe once or twice in his career). Especially since I efile, you can't efile a CD full of 30meg pdf's. Good luck trading & getting taxes done.