Finally, got everything working. Here is a little history.
Have had a TS-440SAT for quite a while but haven't had time to get it going (new house, wife, child, work....the usual.) So I finally got back to it. Ordered an IC-10 chipset, serial cable and USB adapter off of eBay. Installed the chips in the radio (to get a serial connection) and tried to use it.
Here is where the first problem came in. The USB to serial adapter. Word of advice....never use any with the Prolific chipset. I kept getting Code 10 in device manager (Windows 8 and & machines.) Found it, a version of this chipset (HX & HXA) is not compatible with Windows 7 or 8.
Finally found one with an FTDI chipset and it worked right out of the box.
The cool thing with mine (Parallax) is that it has a green LED (for status) and a red LED (for data) that lets me know if everything is communicating. In fact, it did better than an older XP tower with a native serial port.
Loaded up Ham Radio Deluxe version 5 and it immediately connected to the radio. No signal meter (this has an analog meter) but everything else seems to work. No antenna yet and I did not try the transmit but it controlled the radio perfectly.
Now, to get the antenna on the roof.