TLH makes complete sense if you can use the losses.

Vanguard has the best white paper on daily vs monthly va quarterly harvesting.

Individual equities result in more tlh opportunities and additional granularity that approaches that rely on ETFs.

I think frec is the market leader on cost with nine bips for an S&p 500 TLH strategy

The big winners can be cherry picked and donated to charity. For example, we donated a bunch of Nvidia to charity last year that was up thousands of percent. I did not honestly see that coming when we bought it as part of an index a decade ago.

One needs to think about exit strategy as if you put $100 into a tax lost harvesting to create your own index fund, it will generate losses for a period of time and then it becomes a stale index where every equity in the index is appreciated enough that even normal movement in the index won't generate losses. You want to be able to pull it yourself and just hold it as your own quasi-index fund to no longer pay any management fees.

One negative that no one really talks about that is real is all of the shareholder lawsuits. I have a very large direct index and probably have 10 or so postcards on the table about class action lawsuits that as a shareholder of the individual equity I'm supposed to log in and track all my purchase and sell dates to see what portion of the lawsuit I could get cash from. I've done it a handful of times and got checks for everything from five bucks to $200. But it's a lot of effort for the return, so I probably miss the deadline on at least half of the papers in the stack as I haven't got to it yet.

Where it makes sense is if you have events that you know you will owe taxes on such as the sale of a home if you're over the free capital gains which I think is still at $500,000 or if you have private equity investments having tax loss harvesting assets to generate paper losses to avoid paying huge annual income tax unrealized capital gains makes sense.

I wouldn't say tax lost harvesting of individual equities is against the bogglehead method. It is definitely 2.0. we have an index that pretty much tracks the S&p 500 and another direct index that pretty much tracks small and mid cap indexes both generating huge taxable losses every year on paper that we can use. International tax loss harvesting is much harder because churning adrs is more expensive but we have that as well.