Need Network Troubleshooting Help

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Is there a way or program that can help one determine network problems, without needing an IT degree.

I have a large set up for home use. A total of 5 systems running; WHS 2011, Windows Media Center with a couple of Extenders. A couple of workstations, and a remote user that logs in daily to a dedicated workstation set-up as a server. I use VoIP, and a cloud based video security system.

I have a static IP, and have 15x5mb internet service.

Things don't always work well, and they seem to be network related. I just don't know enough to get in there and trouble shoot. Was hoping someone could give me some advice on a fairly simplistic way to monitor and tweak network flow.
 

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