>>>>At what point, on long-term stock holdings, is it advantageous to give up on the capital gains tax advantages by holding through the year, in favor of taking profits, re-loading at a lower price and just paying Uncle Sam the extra tax? <<<<<
Remember, it's not just the difference between the tax rates of long and short term capital gains. If you hold a stock, that principal stays fully invested whereas if you sell, you have to pay tax and can only reinvest what is left after Uncle Sam takes his. This makes a huge difference over time. If you can hold a stock for 20 years, you never pay tax until then. The principal keeps growing, undiminished by taxes, as good as an IRA.
Capital gains on long-term holds is equity that goes untaxed until you sell the stock...
I wrote an example of this effect in Post 9948. This is a huge effect.
Anyway, my big word of caution, is don't let your ego get in the way of good tax planning. It's hard to watch your gains dwindle, and I think most of us take pride in the percentage returned on investment. But, set that pride aside, let those numbers dwindle a bit, and don't give any presents to Uncle Sam.
To follow up on my anecdote on ORCL. I actually sold around 39. Just didn't want to give my gains back. Really was proud of that gain. Still haven't made up the lost ground on taxes. So far I would have been better off letting it ride.
On big gains,50% or more, the tax hit is proportionately big. If you can hold these and leave them to grow undiminished by Uncle Sam, you will do better in the end.
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