Gyroscopic Investing

dualstow wrote: ↑Fri Feb 28, 2025 7:49 am And with that, the ancient yet youthful creature frugal went back into the hollow
of the magic tree where he dwells, not to be seen again until the next solstice,
or a disturbance in the underpinnings of the Universe…

Google says this is Original Content

Google is right in this case

The Tax Loss Harvesting Dilemma

Right now, you have the chance:
An asset with a $100 loss.
Another investment with $100 total profit.

If you sell the losing asset today, you can offset $100 of profit and reduce taxes immediately.

But here’s the catch: in a few years, it’s likely that all your assets will be in the green.
At that point, that loss no longer exists, and the opportunity to reduce taxes on profits simply disappears.

Lesson: sometimes, not using the loss now means losing the chance to save on future taxes. Timing really matters!

Am I thinking about this correctly in terms of HB-PP?

absolutely timing matters .

we delayed selling something one year and they raised the capital gain tax from 15% to 23.5% on that level gain .

it was 20% plus the surcharge on investments

it was a crazy extra amount of taxes .

tax loss harvesting is a double edged sword . you really are just kicking the tax can down the road .

the best deal is tax gain harvesting. that’s is where you have room in the zero capital gains tax bucket to pay no tax at all