I'm in a similar boat as you, having tens of on prem servers hosting our app. Provide options to your customers as to what they should pay and what level of su

I'm in a similar boat as you, having tens of on prem servers hosting our app. Provide options to your customers as to what they should pay and what level of support they will receive. Server goes down mid-day, or mid-night, who's going to fix it? New release is ready for deployment, how is that going to happen? During their business hours, or outside of your business hours? Are they going to need customisations that are out of scope of your product? If you ask now, they'll say "no", but it really means "no, I don't understand the depth of your question". How are you going to handle that? (hint: feature flags and if statements, avoid having separate codebases). We try to automate as much as possible, to the point where we can deploy to a bunch of on prem servers, or a single hosted one, with the same tooling and process. It's not perfect, it's not `heroku deploy`, but it's good enough for us going forward. We use a combo of ansible, docker, and WireGuard to pull this off, but there are paid alternatives if your clients can afford it (like tailscale, replicated, teleport, etc).