A tax discussion, I love it! I never liked the $3-K capital loss as a "strategy" for two reasons. First of all, the tax benefit is minimal (30% tax rate equates to only $900 in savings), plus you need to keep track in future years if the $3-K is exceeded. If the SAME tax software is not used, I've seen many miss or "forget" about the rollover loss in future years. Those who use this as a "strategy" are the same people who failed to cut their trading losses in the first place.
As for the wash sale, this is a basis discussion. You don't "lose" the loss per se, rather the basis is adjusted. Therefore, there is an easy way around this rule (repurchase that same security, sell for a gain, and you can grab the adjusted basis).
