Thanks for the note, N3QE. I was not aware of the commerical products for this very application. I knew there were remote power switches (I even have one I took home from work) but as far as I know it did not have a watchdog mode.
I still think having something that is ham-specific and very hackable is nice, and I really like that I have it connected directly to a Raspberry Pi. That computer is quite powerful. For example, I have an IC-7300, which puts audio and serial over USB. The RPi has USB ports, so I just plug it in, and boom, I have serial that I can remotely access over the RPi. I can remote into the RPi and run ham radio apps directly on it, or I can forward the serial and audio to another machine and work that way. The nice thing is that a little $35 computer that draws < 5W is the whole business: remote access and watchdog. If you want more serial ports, to control other devices, you can also use the RPi's built-in serial port, or plug in more serial devices to the USB ports.
Forwarding serial over IP works well, and of course, if I'm forwarding it, I can easily snoop it and use that to ping the watchdog as you suggest. Forwarding audio over IP works OK for me on the home LAN, but not great over the Internet. I think this is because the software I'm using (pulseaudio) does not do any kind of compression/transcoding, nor is it tolerant of variable delays and dropped packets. I'm going to keep looking for a better solution.
That said, everything works surprisingly well, except for the fact that some ham software just isn't that great on Linux.
Regarding switching DC vs AC, I like having both, and am glad it occurred to me to make the DC connections powerpoles. In fact, I think I will make another version of this board with two or three switches DC outlets rather than one. Then I can power on individual rigs and accessories independently.