Nick, 

You may have done this already, but to be sure let me go through a few steps. If necessary we'll go further.

With a monitor and keyboard connected, boot up to the command line. The enter;

sudo raspi-config

See https://www.raspberrypi.com/documentation/computers/configuration.html for info on using it.

Select Network Options and enter the SSID and Password for your Wifi connection.

While you are there, select Interface Options and enable 'SSH'.

Be sure select 'Finish' and it will prompt you to reboot. Be sure to reboot. At this point, you should have wifi access.

If you don't, then try connecting the RPi to the internet with an Ethernet Cable. See if everything works properly for you. If so, then there is still an issue with your wifi credentials, or the RPi either doesn't have wifi or it's not working properly. 

Let us know. - Mark

Running into the same issue here - I haven't had the map working in probably a month and finally decided to hookup a monitor to see what was going on (I haven't been able to ping even after power cycling it). Same log output as NickFlightX in the original post. After running through the WLAN setup and rebooting, it did start to work until I gracefully shut down the pi and then powered it back up - same errors all over again.

Currently running Buster and i'm guessing an update to the OS perhaps started this issue. Any suggestions? Thanks in advance!

I never heard back from Nick to know what he did to resolve the issue. 

Have you tried my suggestion to him above? - Mark

I did run through the raspi-config settings for the WiFi and SSH - but have not tried an ethernet cable (this is running on a PiZero ... I'd have to dig for the appropriate ethernet dongle lol). That being said - this setup has been running just fine for ~6 months now...and then it just stopped working one day. Probably should have looked into it more on that particular day, but it slipped my mind :-/

Did you reflash the image and now its not working? - Mark

Interesting update - I pulled the map off the wall finally to reimage the SD card and noticed that two of the GPIO pins were bent/touching...figured I'd try straightening them out and booting it up. Amazingly enough that seems to have resolved the issue ¯\_(ツ)_/¯ 

That's awesome! I love the ascii art. Great catch. - Mark

Finally had time to get around to trying out some stuff. Using a ethernet connection, the pi started to pull data for what looks like preloaded airports and such. Pulling a lot of high wind data and cycling through.

With this working, i plugged one string of LEDs in exactly as the diagram showed with power from the bread board. This caused the Pi to go into a boot loop, im assuming for the power the LEDs were drawing.

I then gave the LED string its own power supply and the pi booted, started to pull the data, but no LEDs turned on. I loaded the web editor and could see a way to control each LED, setting all to on did nothing.

 The pi also still is rather unstable and reboots a lot, even with the LEDs on a different power supply.

Send a pic of how its wired. What you are describing is indicative of the RPi being miswired. It happens pretty easy. If you you post a few pics of the wiring, I'll take a look. - Mark

Here is the wiring setup.

Hey, I tried to post the photos twice, but I am getting an Awaiting moderation message on those photos.

I never got alerted. Sorry about that. They are approved now. I'll take a look and let you know what I see, if anything. - Mark