The fact that this supports the Touch Bar alone is _Huge_. Would it be possible to have a basic mode where one makes a one-time payment and has the option to hid all nagging about "Pro" features?
You can pay for the lifetime license, and it will do exactly that.
Enjoyed even the transparency on pricing thinking, but one price that doesn't seem to have been experimented with is allowing a one time purchase that is not an in-app purchase.
In-app purchases make your app unavailable to company employees where the company manages the Apple device using MDM and purchases software using e.g. Apple Business Manager or the older volume purchasing. The $99 option should also exist as a standalone retail version so a company can buy the app for employees.
For small app makers: you might be surprised that a company-managed Mac with a company managed AppleID cannot use in-app purchases. Apple has no way for a company to do IAP for an employee, and in fact the employee cannot do it themselves either. For such users, you must either (a) allow retail app purchase, or (b) have an out-of-band subscription purchase and management, like Microsoft M365 or Adobe Creative Suite.
Whether you do it out of band or as a one time retail purchase, if you do track logins, you should support the simple "Login with" or "Continue with" buttons for Microsoft to hit the 85% of small businesses with identities on that platform, but also Apple and Google. These buttons are easier to add than devs might think. You don't need "SSO" to let most companies log in with company IDs.