If I am very confident that I will be in a lower tax bracket this year than in the next couple years, does it make sense for me to realize some of my gains now? If I still want to hold the same things I can just buy them back after I sell, right?
I'm just trying to make sure I'm not missing something.
My trading philosophy is "fuck the taxes". If I'm making money, then the taxes are a cost of doing business. Of course, I may be losing money to the guberment if I time everything right, but I already receive a preferential tax rate on capital gains and dividends, so meh. I also live in Canada, so we are bred to bend over for guberment...
As long as you aren't losing money, buying back doesn't seem like a problem -- you pay tax on gains no matter what. The problem is if you sell to get the tax benefit, then buy it back. Check what your wash sale (sell?) length is. Last I checked, I think if I sell a holding, I can not buy the exact holding back within 30 days, or it's counted as a wash sale and a loss is no longer tax deductible.