A
Will the WiFi update (if it ever happens) allow the watch to sync with my phone if I leave my phone at home (connected to my home WiFi) and I'm at work on the work's WiFi? Or am I out in left field with my understanding of this?
Yes. That's the way it works. You need to have connected your phone to the wifi first so your watch know about it. Then your watch will connect to the wifi slot and communicate to your phone as long as its connected somehow to the Internet.