How does one decide whether to buy in a normal brokerage account vs. Roth IRA?

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Max out the Roth IRA first since there’s a limit

I’m interpreting your question as what financial assets to buy in a taxable account vs a tax deferred account, such as an IRA account. If it’s better for tax and other purposes to have a lower adjusted gross income, then you would buy stocks that do not pay dividends but have great potential for stock price increase in the taxable account. The tax deferred account would be the place to buy dividend paying stocks with a strong balance sheet so that the risk a loss in stock is minimized. Many mutual funds are not good choices in a taxable account since you have no control over the income they dump in your tax return. It’s not an issue for the tax deferred account.

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