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I would build a test server at my home with a software config. that is close to what your "real" server will use. I would put a couple sites on it and see how comfortable you are changing configs, settings, etc.
Find some people that could help you by trying to break into it to find the holes.
Get familiar with server admin software. Introduce yourself to unleashed.
Surpass servers are semi managed. So, they will help you succeed. If you get into a jam they can help you out of it. That is SEMI-managed. It is your box.
There are lots of server management software out there that you can use to monitor the services.
Introduce yourself to unleashed. There are other users that would be eager and willing to help youwithyour conversion.
Caution is the key.
Surround yourself with people smarter than yourself.
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