I think the key difference between Directus and Sentry is that the restrictions Sentry put in place are directed at folks who want to build and sell their own error reporting service to software companies (and obviously commercially exploit the work they have done). In the same way that Redis went down the route of SSPL with the aim of impacting cloud services with their own Memorystore product that just resold Redis. That meant that most users were unaffected and your 10-person company using Redis as a cache to power their website could continue to do so. We continue to self-host Sentry and we're incredibly grateful that that's something we do have the option to do.
I don't have much of an issue with companies taking that approach. I actually genuinely wouldn't have an issue with an AGPL Directus, or SSPL (and releasing all of the plugins we developed internally). But that's not where Directus ended up and so we'll eventually either move to something written internally or an alternative that actually is FOSS.
> With an delayed-open-source-license w/ a usage grant that allows all the community members that historically contributed to use it for free, we found a balance between keeping it as open source as possible, while making sure large companies that make a lot of money using it are required to contribute back.
I do want to reiterate that a specific "total revenue"/"total funding" figure != "making a lot of money" and I don't think your license captures this nuance at all, today.