The best way to learn is to get in there and just do it. Running the serer itself is going to allow for learnable situations.
I recommend a VPS or dedicated server from a vendor that allows you to reinstall if necessary. A good way to have "Training wheels" (honestly can't really even call it that, you'll probably use it for life) is to add something like cPanel. That takes the general purpose server and turns it into a web hosting server.
I'd recommend the following general plan:
1. Rent a server with cPanel. Before anything else, get familiar with the tools like IPMI (or for VPS, the console) so that you know what your tools are if anything breaks. Reboot it a few times. Reinstall the OS. Install a couple different OSs. Familiar? Move on.
2. Run updates on the OS. Install and harden cPanel. There are plenty of tutorials out there for hardening a cPanel server, pick any of them and follow it. That will walk you through learning some basic commands and where things are in the control panel. The other nice thing about cPanel is that at this point, almost any problem is Googleable.
3. Set up a test website or two. This should be the most straightforward part with your background.
That should give you a good feel of what you're working with. If, at that point, you don't feel comfortable, don't put production sites on the server. Keep playing with server settings and learning what does what.
If you feel comfortable with where you are, then proceed with your customer sites.
- VPS, Colocation, and Dedicated servers
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