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Personal Investments • When to sell holdings with long-term gains to streamline portfolio

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How should one think about selling existing holdings with long-term gains to streamline their portfolio (e.g. VTI + VXUS + MUB)?

I recently transferred all of my Wealthfront assets "in kind" to a Vanguard brokerage account, and now have a lengthy list of various holdings. All of these holdings have gains (no losses), so selling any of them will incur some level of tax.

I understand the logical selling sequence with regards to taxation (short-term loss largest to smallest -> long-term loss largest to smallest, etc.). What's unclear to me is how to determine if it's better to leave it invested in the existing fund as is (until a loss occurs, if ever?), or to pay the tax to streamline investments to a small number of desirable funds.

Thanks for any clarification. Learning as I go.

Statistics: Posted by dayfornight — Wed May 08, 2024 9:10 pm — Replies 5 — Views 455



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