Let's say that I bought 500 shares of company ABC while the stock was doing well, and paid $10 per share for a total of $5,000. Then over the next year (while I was overseas, let's say) the company tanked and dropped to $2 per share. Since I had no safeties in place to trigger a sell off, I now own 500 shares worth $1000.
After I get over my initial frustration at the loss, I realize that even though only at a fraction of it's initial value, ABC is now regularly fluctuating between $2 and $3. I decide rather than taking an immediate $4000 loss, to start trading on smaller increments and take advantage of the regular fluctuations in price.
I purchase another 100 shares of ABC at $2, and then sell it a week later when the price hits $3. Because I am calculating capital gains using FIFO, I record a $700 loss on the 100 shares, but now I am still $100 richer. Assuming the price shortly turns around and hits $2 again, I repeat the process again and over the next several months I (hopefully) begin to recover a portion of my losses, all while avoiding short-term capital gains.
Neglecting transaction fees, are there any drawbacks to this approach?