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I pretty sure I need some help...
In early 2006 I sold some shares of one of my Vanguard funds to purchase other Vanguard funds. Now that it is tax time, I THINK I want to specify specific lots to maximize my losses so as to offset other capital gains. The bookkeeping issue is not a problem since I have all the details thanks to Quicken. So here are my points of confusion...
Assuming this is the right thing to do, was I supposed to specify the lots at the time of sale? I asked a Vanguard rep this question and he said no, that I simply need to send them a letter stating which lots I intended to sell an that would become a part of my account's record. The answer came after being put on hold for a long time, so I don't have a high level of confidence in this answer.
Is specifying specific lots the right thing to do? Yeah, I'm sure it depends on my situation but I need help understanding when this is a good idea vs. a bad idea. As it stands now, the losses are significant enough to rack up carryover for the next couple of years. I intend to RE in early 2008 so there will be no significant earned income for the year (not even sure this matters).
Help!
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