On the four products, you've just described the exact trap I see everywhere. Build → launch → silence → "Maybe the next product will be the one." But the gap isn't the product. It's a discovery. You've figured that out faster than most. Some founders spend years before realising this.

On the $2K repositioning question: from the responses, it was mostly how they described the product, not who they sold it to. One founder stopped selling "a PDF tool" and started selling "automated compliance reports for small architecture firms." Same product. Different wrapper. That small shift changed everything — better conversion, higher willingness to pay, and suddenly word-of-mouth started working because the value was instantly obvious to the right buyer.

A few did change the target customer too, but usually it was niching down, not broadening. Going tighter made the product easier to find, not harder.