As someone else who has been happily running a small business on dedicated hardware with a managed hosting service for years, I share some of the GP's scepticis

As someone else who has been happily running a small business on dedicated hardware with a managed hosting service for years, I share some of the GP's scepticism about modern cloud hosting. Modern platforms should remove most of the complexity of operating routine infrastructure and allow you to focus on your business logic, but it doesn't always work out that way. Just the fact that your VMs have a significant chance of being forcibly shut down with little notice is a significant downside, for example. As a solo operator, you now have to arrange all the automatic scaling and failover configuration on your cloud host as well (possibly at considerable extra cost for capacity you might not be using 99% of the time) and you have all the 24/7/365 monitoring problems that OP was asking about. Cloud services are also notorious for obfuscating their pricing so it's hard to work out the TCO. In my experience, arguments that cloud hosting works out much cheaper overall tend to be based on rather optimistic assumptions. It might be true if you lease some VMs at carefully chosen sizes and then set everything up yourself including scaling things down again any time you don't need them. However, once you start using the automatic services that actually do something for you beyond supplying a machine on demand, the prices might jump 3x or more (sometimes much more, like orders of magnitude) compared to ordering the equivalent basic resources and setting the same functionality up manually. Then there are the security and compatibility updates. The basic cloud services tend to be provided as-is and it's up to you to ensure everything gets updated when it needs to be. Or again, you might be able to get a more automated service that does some of this for you, but it will come with a pricing premium. Meanwhile, a solo operator using a more traditional managed service probably doesn't have to worry much about any of this, because those services will often be happy to take care of things like setting up your redundant database servers or monitoring the security mailing lists and applying emergency patches very quickly so you don't have to. That's the level of individual service and advice they tend to offer to distinguish themselves from the generic cloud hosting services. Obviously you do pay extra for that management service compared to just a basic hosting arrangement, but whether you pay more than you'd have paid trying to do all of it yourself on AWS or Azure or even DO is another question.