I make a great living selling Cursive (https://cursive-ide.com). I use perpetual licensing with a year of updates, $99 for personal and $199 for commercial licences. Renewing for more updates initially costs half that and then goes up linearly to 75% over the first year after update period expiry. I also have a free non-commercial licence for OSS work/student work/personal hacking.

I figured that I would sell about the same number of personal and commercial licences since there are still a lot of hobbyists dabbling with Clojure, but in the end the vast majority of my sales and revenue are commercial licences. Most of my revenue is new licence sales, but I see a fair number of renewals too.

Short answer: a good path for monetization is just charging for your work. It's kind of old fashioned but it does work, even for dev tools. If your product solves a real problem companies are willing to pay to make the problem go away, especially if your product is more polished than the (presumably OSS) alternatives.