"In many ways, I think I picked a great stack to move quickly and ship things. However, considering all the time spent debugging some of issues that stemmed from using more cutting edge infra providers, next time I'll more carefully consider setting up parts of my infra with a more traditional solution like AWS."
It really depends on which parts of AWS you're using. Spinning up a bunch of EC2 instances and treating them like colo'ed servers has pretty much always been boring (other than the excitement of not having drive to the DC when you need to reboot something).
Tend to agree, though I don't always practice it. Boring is also subjective, even if it's a metaphor for mature.
The same sort of arguments could be said for "choose what you know", "choose what you understand", "choose what you can hire for", "choose what you can afford".. the list goes on.
Like most things in life there are no cheat codes.
That right there is the rationale behind the "Choose Boring Technology" movement: https://boringtechnology.club/