OP here - based on the feedback, I’ve switched boringBar to a perpetual license for personal use: https://boringbar.app

It’s now $40 for 2 devices and includes 2 years of updates. After that, you can keep using the version you have, or choose to pay for updates again later.

For businesses, I’m keeping the existing annual pricing.

A lot of the comments on pricing were fair, and I appreciate people being direct about it. I still care a lot about long-term maintenance for an app like this, but I think this is a better balance.