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by nostrademons 2714 days ago
The tax reporting is also pretty nightmarish. I have a friend who once decided he could mimic an index fund without the fees by buying individual stocks in the same proportions as the index (I think his broker offered a free trades deal or something, otherwise this is an obviously bad idea). His Schedule D that year was about 60 pages long, and he decided never again. Of course, it took him years to finish unwinding all the positions and reporting all the taxes, since many times you're left with a small fraction of a share once dividends have been reinvested.
2 comments

Buying individual stocks in proportion to the market-cap index is possible today as a service, and advertised by Wealthfront as "direct indexing" or stock-level tax-loss harvesting

The small tax advantage is that you can sell individual stocks for tax-loss harvesting. Fisher advisors also offers this for HNW folks.

This article criticizes this as a lock-in for wealthfront, unlike funds which can be easily transferred to brokerage "in-kind" (without 500 separate securities, or selling as a taxable event) * https://medium.com/@wwalser/the-trap-of-wealthfronts-direct-...

RIP Bogle, making the world a fairer place rather than being a billionaire. I'd like to bike from Philadelphia to Valley Forge again to make pilgrimage.

Oh man you definitely want to turn off dividend reinvestment in taxable accounts, the tax reporting makes it impractical. Take dividends as cash and then roll that cash into regular periodic contributions (or distributions).