I have an 'iTeadMaple" (from iTeadStudio) and it works without needing to disconnect and reconnect
However I get the feeling when using it, that the bootloader seems less stable than the one in the Maple Mini
The bootloader for the Maple is not quite the same as the Maple mini. I think its shared code, but with compile time switches, so there could be some issues with it.
I also agree with Ray. I have damaged one STM32 USB connector by unplugging and reconnecting, and had to resolder it
Try moving the USB cable while its plugged into the Maple and see if Windows disconnects and reconnects, if so you have a loose connection on the board
Re: Windows drivers.
How are you installing them, I presume you use the windows drivers folder in the repo, which was a contribution by another user, and works fine on Windows 7 and from what I understand also works on Windows 8 and 8.1 (though I have not tried it myself)