I wanted to follow-up on this. I now have a fully-outdoor PiAware install.
I purchased a SOCKiTBOX (medium size) and installed everything outside. I have a reasonably out-of-the-way and sheltered spot for this by my deck. It looks to be very water-proof. The official Pi 4B operating temperature only goes down to 32F, but I found some forum posts claiming they still worked fine at -40F so it might even work in a Minnesota winter.
The CanaKit power cable, switch, and transformer are all tucked inside, only a weather-proof extension cord comes out. It is hard to see in the picture here, but there is some compressible foam where the cord leaves the SOCKETiTBOX making what appears to be a water-tight seal. I am using a case with passive (no fan) cooling for the Pi 4B. Using wi-fi for data.
Here is everything tucked away with only the power cable and coax coming out.