I posted a thesis earlier :) but thought I pull out something and ask a more pointed questions.
In March 2006 (no clue what version of Quicken I was using then) I recharacterized 14 months of Roth IRA contributions to traditional IRA due to my exceeding the Fed guidelines for income. My brokerage statement broke that up into two transfers...all of 2005 as one and the first two contributions in 2006 as the other (kinda, I can't get the math right but I'll assume the brokerage was right...in the long run it's irrelevant), so I did the same in Quicken to keep the records clean.
So in the old account I used the "transfer to new account" transaction type and selected "last in" for lots since it was the last 14 transactions I'd made in error to the wrong account. In the new account that somehow translated to 39 transactions (since the two transfer transactions accounted for 14 contributions, all at probably different share prices, one would expect this to create at most 14 transactions in the new account, not 39), each with the date acquired, a share price, and an amount. One would assume the "amount" would be the cost basis for the shares. Not so sure. For one thing, the dates for 6 of the transactions go back to 2001/2002. Using "Last-in" should not have transferred shares acquired before 2005. Second, no idea why I ended up with 39 transactions from the 14 that transferred (although the total shares came out correct).
Lastly, if I have Quicken gonkulate a cost basis report for the shares that transferred into the new account, I get $4881.85, yet I made 14 contributions of $333.33 ($4666.62). Can't figure out how QUicken and I are off by 220 bucks or so.
If anyone has ideas I'm listening...