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Server hardware has become much more reliable over the years, Linux and FreeBSD has matured and is less prone to crashes.
Learning is not too difficult, mastering takes many years. I've been working with various incarnations of *nix for over 25 years and still wouldn't consider myself expert.
Some of your questions are really 'how long is a piece of string' , do you want to just run your own server / VPS or do you want to become a guru ?
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