Are two options ever too similar for taxes?

In my opinon, https://fairmark.com/ is a reputable site for tax advice. Here's an abbreviated version of their take on the wash sale possibilities involving stock and options:

If you sell a stock at a loss, it's a wash sale if you buy substantially identical stock within the 61-day wash sale period. You’ll also have a wash sale if you enter into a contract or option to buy substantially identical stock.

Example: On March 31 you sell 100 shares of XYZ at a loss. On April 10 you buy a call option on XYZ stock. (A call option gives you the right to buy 100 shares.) The sale on March 31 is a wash sale.

It doesn’t matter if the call option is in the money. You’ll have a wash sale even if you never exercise the option and acquire the stock.

You can also turn a sale of stock into a wash sale by selling puts. It applies only if the put option is deep in the money and there’s no precise standard to determine that. The rule applies that when you sell the ITM put and there is no substantial likelihood it will expire unexercised. IOW, selling the put option is roughly equivalent to buying the stock.

Example: On March 31 you sell 100 shares of XYZ at a loss. On April 10 you sell a put option giving the holder the right to sell to you 100 shares of XYZ at a price substantially higher than the current market price of the stock. The sale on March 31 is a wash sale.

As an ITM put seller, you participate in the up and down movement share price, unless the price moves higher than the strike price. If the strike price is high enough, the chances of that happening are small and you’ve simply found a different way to continue your investment in the stock.

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EDIT: Add'l Info:

Another reputable site for tax advice on trading is Greentradertax.com . Re wash sales, they cite IRS Pub 550:

A wash sale occurs when you (a taxpayer) sell or trade stock or securities at a loss and within 30 days before or after the sale you:

• Buy substantially identical stock or securities,
• Acquire substantially identical stock or securities in a fully taxable trade,
• Acquire a contract or option to buy substantially identical stock or securities, or
• Acquire substantially identical stock for your individual retirement account (IRA) or Roth IRA.

They also add:

IRS regulations for wash-sale losses require taxpayers to calculate wash sales based on “substantially identical” positions. That’s different from the rule for brokers that require “identical” positions. This can be a challenge for active traders who trade stocks and options, or just options but with constant changes in exercise dates - these are substantially identical positions.