Let’s face it: web hosting is a market for lemons. There are so many providers. New categories are emerging. Borders blur. Microservices everywhere. It’s complex. It’s noisy. It’s hard.
I used to work with providers that offered sharing hosting that could be administered with tools like Plesk and cPanel. The biggest drawbacks of shared hosting are that these environments don't get updated regularly and you can't really install all the tools you need. We've also had serious troubles with performance in some cases (presumably caused by other users on the same machine).
Thanks to all the excellent resources on server management (like serversforhackers.com and sysadmincasts.com) and tools to provision them (like Forge) I feel confident enough to administer my own boxes. A little over a year ago all new projects at Spatie are hosted on DigitalOcean. We have multiple droplets running and haven't run into any of the problems we faced with the old school hosting providers.