>> Tools you pay for that feel overpriced
I get your thinking here - free market spots a gap and competes on price. But personally I think this is a "poor" business strategy.
Firstly, competing on price is a race to the bottom. There's always someone who's prepared to offer it for less. And that always means the offering ultimately gets worse over time.
Secondly if you go thus route you attract customers who are "price sensitive". They'll leave you as quickly as they joined for someone who offers a lower price. In other words you are self-selecting the worst possible kind of customer to have.
Thirdly you send a signal regarding quality. A $5 product is obviously worse than a $100 product, because if the $5 -could- charge more they -would-.
(Hint: for VC funded companies the customer I the VC NOT the person paying a subscription. So be careful comparing your pricing to VC company pricing if you are not VC funded.)
Yes, look for pain. If you make something good charge more, not less, than incumbents. Build a customer base of people who are quality sensitive not price sensitive.
30 years ago I had a product on the market at $199. It sold well, validating the market space. A not-quite-as-good competitor appeared for $99. He made some sales. I was tempted to reduce my price. An old head told me otherwise. Sales wise we'd say things like "you get what you pay for". We outsold the new-guy. Which meant we had lots more revenue for support, docs, polish and so on. Today we charge $399. The competitor folded after a couple years.
We aimed high, charged a lot, and focused on delivering quality. We attracted loyal customers who appreciated quality more than a few $ saving. 30 years, and 50 products later, we continue to dominate our space.