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It sounds like your device could be getting different IP addresses from the DHCP server each time it starts up the WiFi connection. If you were using the wrong IP address on the PC, that would explain the "No route to host" error messages.
If you get the sh_ivtool package from the Developer section and install it to /mnt/ext1/system/bin, edit the applications/sshd_start.app script to uncomment the "#SH_IVTOOL=.." line, then sshd should pop up a dialog saying what IP address and port that it is listening to. That way, you know what address to point scp/ssh at on your PC.
I'm also adding the same functionality to the utelnetd package. I should have that download ready shortly after this.
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