The Telnet from host to server garbled characters is a good thing. We know that the server is listening on that port.
Can you look at the nsclient.log file on the windows host and post the errors here?
Can you upload the latest nsclient.ini file to this post?
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2015-08-25 11:49:50: error:D:\source\nscp\modules\Scheduler\Scheduler.cpp:122: Failed to submit check_work: Error: Failed to connect to: 192.168.253.107:5667 :A connection attempt failed because the connected party did not properly respond after a period of time, or established connection failed because connected host has failed to respond
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2015-08-25 11:49:50: error:D:\source\nscp\modules\Scheduler\Scheduler.cpp:122: Failed to submit check_work: Error: Failed to connect to: 192.168.253.107:5667 :A connection attempt failed because the connected party did not properly respond after a period of time, or established connection failed because connected host has failed to respond
Under your allowed hosts, is the IP address AND the hostname there? What happens if you try to use exclusively IP addresses instead of the hostnames?