Syncing with iTunes over wifi doesn't work

My iTunes sometimes does not recognize my iPhone... but sometimes it does. When I click to sync it will start but it will get an error eventually like "Sync failed to start" or "Unknown error -50".
I am not sure why iTunes will not sync. It used to work, but lately it hasn't been.
I put a bunch of new music on iTunes yesterday from old CD's I had and when I went to sync it showed it did, but when I went to play my music on my iPhone all the songs were just grayed out so I couldn't click on them....
so I used to USB cord and it synced fine...
So can it not send that much data over wifi or something?
I'm using iTunes on my Windows 7 laptop. I also have an iPad it won't sync with either.
Thx.

Which application are you trying to use?
The manual mentions setting up an NMEA port where you post describes a COM port. In the printing world a COM port is a USB physical port or oldschool Serial port. These may not be the same thing which might explain why your app is not working.
Lookup your installed ports (WinXP):
1. Navigate to Start > Run
2. Enter "cmd"
3. Click OK
4. Enter "netstat -a"
5. Scroll through the list and review all available ports
If your port is not mentioned above by the port number you selected from the Wi-Fi over GPS screen then it is not active and will not be useful for your apps. From the manual it looks like the default port number is 10110.
I would check the support site for your application to see if it is compatible with NMEA. They might have more steps for you on how to configure your app to utilize the GPS over WiFi feature of the MiFi.

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Welcome to Apple Support Communities.
The article linked below provides a lot of great information and troubleshooting tips which you can use to resolve the Wi-Fi issues that you’re running into on your iPad since upgrading iOS.
iOS: Troubleshooting Wi-Fi networks and connections - Apple Support
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The manual mentions setting up an NMEA port where you post describes a COM port. In the printing world a COM port is a USB physical port or oldschool Serial port. These may not be the same thing which might explain why your app is not working.
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