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As an on-and-off DO customer learning how to use Linux I find the documentation they've creates (payed ICs to create, I think) extremely useful and consistently of decent quality. When I see them in a Google search for an issue I'm always excited.

Are you over $500/month spend with DO? They offer a different tier of support at that point which has been solid in my experience.

totally. I mentioned this in another comment but it feels like a skill floor/ceiling thing to me.

AWS/etc heavily reward you for investing time/money/etc but can be a bit more difficult to get started with without investing resources immediately, whereas DO is very easy to get up and running on but can be difficult when you encounter anything more complex.