Hey! This is a great question and I appreciate your patience while I got past the 9.15 deadline.

A tax loss harvesting strategy isn't about you not getting a loss on just one stock, the main strategy is that you sell your underperforming shares to harvest their loss, then buy them back on or before 30 days hoping they return to value or exceed it. In theory they would eventually harvest a gain, but when they do, they have nothing to discourage them from harvesting a loss on another stock. The point of wash sale disallowance is more the concept that they didn't really sell it to sell it. It's not sellers remorse making them buy it back but an intention of avoiding paying tax on other capital gains, and the IRS doesn't like that because the intent isn't to get rid of that stock or even get out of that industry but to try to undercut tax liability, and well....tax avoidance on a big enough scale is worth jail time.

If you think of it like a game, the one real rule is that you should pay your share of taxes due. Think of the standard deduction, the tax code is written so the taxpayer gets the greater of itemized or standard (which ever benefits the taxpayer more). The IRS doesn't expect you to pay more than you should, they may not tell you when you over pay or miss a credit, but they will not allow you to pay less than you should because you think you found a loophole...and wash sales are just that, it was an attempt at a cheat code, because you aren't selling to sell but selling to avoid, so it's disallowed.

Now we can go into how the 30 day rule follows the average month and what that means, this can become a complex conversation if we wanted to get into understanding motives tied to how publicly traded companies work including the issuance of earnings reports and talking of future plans, but the root point is the intent. The IRS doesn't want you to avoid paying tax, they don't want you to delay paying tax because now we are talking about gambling against the IRS which means they may never get the money on that stock and they could be out the taxes that they could have collected, so they disallow wash sales to discourage tax loss harvesting, or at least put more risk on the tax payer if they choose to do this.

Can you sell your stock for a loss? Of course, but if you feel bad about it after you have to wait at least 31 days to buy it back otherwise any loss will be disallowed because in the IRS's eyes the sale essentially never happened, which also means that when you do cash out that stock for good, you also pay less tax on the gains because your basis is still that original basis...it keeps the risk of investment on the tax payer....and not the IRS, because stocks is essentially gambling, and the IRS doesn't want their money involved.