Tax loss harvesting question

[DrJohn]

From Bogleheads (https://www.bogleheads.org/wiki/Wash_sale):

The Vanguard Total Stock Market and Vanguard Large Cap Index track different indexes, but the returns are similar, and as such, they are good alternatives for domestic holdings. Vanguard Total International Stock Market and Vanguard FTSE All World Ex-US also have similar performance while tracking different indexes.

Is it worth switching between the funds above to generate a tax loss?

One key thing to think about is that we pay a lot of income tax right now and this will be retirement money to be used in a couple of years...so gains realized in future will be taxed at lowest rate.

[spud1987]

Another option for VTSAX is exchanging to the SP500 index. I've been doing this the last few weeks.

[TheOldestYoungMan]

It depends on your post-retirement withdrawal amounts.

As a rule of thumb, I expect to withdraw so little that I'll have no earned income taxes, only capital gains, so anything I can do to get back income tax now is worthwhile.

However, that is of limited utility as my income tax burden is getting pretty close to zero.

If you "pay lot a of income tax" you may be in the 15% bracket in retirement anyway, and so lowering your cost basis for the future may not be sufficiently offset by the extra cash now.

For almost everyone what you describe is a good idea, but enough people fall into the second category that I think it's important to encourage you to do the actual math or post more details so we can do the math for you.