Much of this matches my own experience. A few thoughts:
1. Cost tracking meetings with your finance team are useful, but for AWS and other services that support it I highly recommend setting billing alarms. The sooner you can know about runaway costs, the sooner you can do something about it.
2. Highly recommend PGAnalyze (https://pganalyze.com/) if you're running Postgres in your stack. It's really intuitive, and has proven itself invaluable many times when debugging issues.
3. Having used Notion for like 7 years now, I don't think I love it as much as I used to. I feel like the "complexity" of documents gets inflated by Notion and the number of tools it gives you, and the experience of just writing text in Notion isn't super smooth IMO.
4. +1 to moving off JIRA. We moved to Shortcut years ago, I know Linear is the new hotness now.
5. I would put Datadog as an "endorse". It's certainly expensive but I feel we get loads of value out of it since we leaned so heavily into it as a central platform.
There's a big difference between runaway costs and these costs over here, which are 10-20% higher than we think makes sense, especially compared to what we're spending over here. Let's spend some time figuring out how to reduce those costs. You should be doing both - belt and suspenders.