If you google for some standard server maintenance problem (e.g. migrating from Apache to nginx), it's usually DO which is ranked first. Their posts are relatively high quality, and there are a lot of them, enough to cover many common problems. For example: https://www.digitalocean.com/community/tutorials/how-to-migr...
It doesn't show annoying pop ups, anything like that, but after visiting those pages many times you might decide to give DO a go. Well, that's what I did.
Also, some people say that similar cheap VPS providers exist for a long time and what DO did was put a nice simple UI. That proves that to create a successful product, you don't need some new complicated features that your competitors do not offer. Making interactions with the system easier, improving user onboarding process by reducing friction can go a long way.