A high price in a font won't sink a business as a high price in truffle would for a Michelin chef... The price of a font for a business is extremely negligible... Or again you shouldn't buy it if your business is too small. And if it's that small you should be able to justify the value added by buying that font as truffle does for the chef.
So we are back at what OP said.
It doesn't fall apart, you have examples that actually match it. Marketing boutiques of website creators match the 3-star Michelin analogy. High budgets from their customers (think LVMH) are the norm. And they will love and understand paying X for a font. In fact they will almost expect this type of thing in the design process.
At the end of the day if people don't see the difference and the value between a free and a priced one, then they don't need to steal and can just use the free ones. There are plenty of amazing free fonts anyway some being the actual roots of many paying ones, and the gold standards.
Maybe it won't sink the business, but prices were bad enough for IBM to cough up the money to grow their own truffles (of IBM Plex variety).
Well the analogy falls apart because (among many, many other reasons) the people eating at Michelin rated restaurants, especially 3-star, are completely insensitive to the price. It will cost whatever it costs and there will still be a long wait to get a table, if you even can.
So rather than pretending we're talking about truffles, let's just talk about fonts directly without strained analogies. Fonts, which the majority of people don't even recognize. 90% of people don't even know what a foundry is. Your average person can't tell the difference between any two fonts if they're both sans-serif or serif.