Brokerage & Tax Question

manlymatt83

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Hi all,

A bit off topic, but hopefully someone can chime in.

I'm currently with Sharebuilder, but I find it's a bit limiting. Though, so far this year I've done quite well, but I've build up 15,000 shares of one stock. That dollar cost averaging is great (Automatic $4 investments on Tuesdays), but I can't set a limit price. I've seemed to have found out that it's almost better for me to MANUALLY buy shares and pay the $9.99 full trade commission than it is to automatically invest on Tuesday's for only $4, as that $5 difference can be offset by setting limit orders. Also, Sharebuilder charges extra for options ($1.50/contract, and I like to write covered calls a lot!), and 2.5 cents for any share over 1000 shares (ouch!). So all in all, I find myself leaning towards moving to TD Ameritrade.

Among the warnings I've read is that people who have moved away from Sharebuilder (which does weekly recurring investments) and into the "Non automatic, invest when you want" strategy tend to get greedy and do more and more trades, and end up losing money. I'm trying to stay away from that attitude, but I don't think it's worth the risk of staying with Sharebuilder and not having the features such as stop % orders (which has saved me a bunch of times - I don't want to sit there and change the stop loss price every few days, even on long term investments). Thoughts? Anyone agree? I think you can still be a long term investor vs. short term trader and still use something like TD Ameritrade to your benefit over something like Sharebuilder (even though Sharebuilder is meant for longer term investing).

Which also brings me to my next point - moving my portfolio. Sharebuilder doesn't participate in ACAT, so that scares me, because it'll take 4 weeks to manually move my assets. What if the market dives during that time? I can't have any stop losses set. I've been thinking of selling my positions and then re-buying them back at Ameritrade, but that also has tax implications. Which also yields my next (and second) question of the thread:

In October 2008, I was just starting, so I made a bunch of stupid buys. In early February, I sold all those stocks for a total of about a $7,000 loss. Ouch! But, I smartened up, and in December 2008 (still in 2008!) I bought about $2000 worth of stock, which is now worth about $10,000. So, if I look at my gains and loss tracker (realized positions), it says I have a short term capital loss of $7000. But if I look at my unrealized positions (since I still hold the ones in December that were all good picks), I'm up about $8000. My accountant says right now, if I hold, then come tax time in 2010 (for 2009 year), I'll be able to declare a $3K loss, and then another $3K loss the following year. However, I'm wondering: if I sell the $7K worth of stock I have now, will that immediately offset my losses, and I won't be able to deduct anything, but I won't have to pay any taxes on the $7K profit either? Or does the $3K rule still apply, and I'd still have to pay taxes on the $4K net? What if I hold these stocks until December 20th of this year - at that point, the losses remain short term capital losses (October 2008 -> February 2009 = 4 months), but the gains would become long term (December 2008 -> December 2009). Does that fare differently?

Thanks for any explanations on any of these two items! FYI, I'm NOT considered a pattern day trader at either Ameritrade or Sharebuilder, and so far, all of my equities are still at Sharebuilder (I placed a few trades here and there at Ameritrade to test the waters). FYI, this is US Tax law, I'm a United States citizen.
 
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