Is it a must to know how can I deal with Windows server when I want to host my ASP.NET on Windows VPS? It would be helpful if you can explain in a bit of detail.
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Should I know how to drive a car when I am driving one?
Share web hosting is like a taxi - you get in, say where you want to go and the driver takes you there.
VPS is like driving yourself. If you dont know what you do you end up on a tree or dead. If you can start the car.
Stuff like security, general performance and system monitoring, all that are up to you (or you hire a driver, known as managed VPS - an admin does it for you).
So, in general - yes. You should know what you do before doing it. You should know how to work with Windows server before using it on a VPS - or pay someone who knows.
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2This is one of the better car analogies, +1 :-) – ThatGraemeGuy Feb 16 '11 at 07:28
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1Well, he knows what he is talking about, he (TomTom) is the navigator :p – Lekensteyn Mar 06 '11 at 20:27