I am using Windows 98 SE and an RS-232C serial cable to program a new radio. To do this I have to run Virtual PC on my Mac, use a USB serial adapter, tell VPC to use that adapter as COM2 on the Windows box, and manually set all kinds of options for this "serial port." Then I get to use a 1996 quality Windows application to read spreadsheet type data and very slowly write it to the radio over the serial cable. This works approximately 40% of the time.
I have no reason to believe it would work more of the time if I had a PC laptop running Windows natively.
There's a place where the wonderful Web 2.0 Nifty Gadgets Open Source Free Extensible Modular Optimized World of Today ends. It's the place where you have to hook your computer up to a device, any device: radio, weather station, medical equipment, anvil, surface to air missile, automobile, inclined plane. Immediately you're struggling with some antedeluvian program written by a semicompetent nerd who hates humans, using ten-year-old tools, which is never ever going to be updated. The interface is guaranteed to be opaque, features will be missing or greyed out forever, and there will be no tech support of any kind. You are, at this point, in Hell.
I wish I knew how to write software. Half this shit has open protocols and is just begging for someone who isn't an assclown to write something useful using exciting new technologies like "USB" and "user interface."