What are the best tax tips and tricks you wish you learned sooner?

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Max 401k.


Once your income tax bracket is higher than you expect it to be in retirement (remembering that a portion of retirement $ with be at lower LTCG rate!),
Trad is better - assuming you also invest the tax savings it gives you right now.

As SC1 says, I also have Roth IRA, via backdoor, to be able to save more.

Buying rental property. Thanks to allowed depreciation, the cashflow is practically tax free!


1250 recapture is more than cap gains.

Audit lottery.


Tax loss harvesting.

Cost segregation on rental properties.


Learning how and when to take losses

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