The missing help file sounds like a corrupted download or installlation. Try uninstalling the program, then re-download and reinstall.
The time-out could be caused by a bunch of things. First, ohm out the cable and make sure pins 2 thru 8 all connect straight through. Some cheaper serial cables only have 3 wires, for TX/RX/COM. I believe the TM-D700 needs all 7 wires. Are you using a real serial port on the computer, or a USB port with a serial adapter? I have recently found that for whatever reason, my Keyspan USB to Serial converter will not work with the TM-D700.. I have to use my old laptop with the real serial port!
de Tom, KA1MDAwww.ka1mda.org