Thanks for the useful suggestions everyone. I haven't had a chance to go back and troubleshoot too much this past week but hope to have some time this weekend.
One thing that I noticed when looking back at the WiFi settings (when that was suggested) was that the country code resets (or doesn't set in the first place?) when set through the raspberry pi configuration (the prompt that opens during first boot up).
On reset, it goes back to "no country selected" (or similar). I had read elsewhere (can't find it now) that a lot of the connectivity is disabled until the country code is selected. So I think the country code not saving/being set could be the culprit (or at least something that isn't helping).
That seems to have fixed the country code (1. actually gets written to wpa_supplicant.conf unlike through raspberry pi configure 2. stays the same through reboot), but then I couldn't figure out how to turn the network-manager back on... I tried all sorts of start, enable, and restart commands, as well as rebooting. Googled solutions didn't seem to turn it back on, and I hadn't had a chance to tinker with it more past that. So in it's current state, it has the right country code but the network-manager never turns on, so I can't test if that was the issue or not.