> So the problem you have is that you think (but don't know) that your product is much more valuable to your users than they think it is (since they're only willing to pay $20 for it).
No, the problem is that whatever you think your product is worth is irrelevant. What matters is your costs, that puts the bottom on the price, unless you want to burn cash for growth. Your customers expectations are the ceiling.
Of course all your customers are not alike and maybe there's 10% that would pay so much more to outperform the other 90% in revenue. That's when upselling comes into play, or maybe you want to focus only on the 10% entirely.
> If your program is actually worth thousands of dollars to the user, but they're only willing to pay $20 given their current knowledge, you don't want to tilt their expectations by "a little bit". You want to tilt their expectations by a couple of orders of magnitude. Which, as noted above, is not doable by hacking how your pricing is presented on a web page.
It's not doable at all. Nobody who expects to pay $20 for something will shell out $200 for it, unless they have looked everywhere and figured that everyone else charges in the same ballpark, or that you are the only option and they really need your product.
Anchoring isn't magic, it's the same kind of trick that makes $9.99 appear substantially cheaper than $10.00. It'll give you a slight boost.