That looks solid. One additional thing I would add:
# Enable logging
logger:
level: VERY_VERBOSE #DEBUG is the default
Need to run my son to hockey – back online in few hours – will check back…
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Interesting. One source for searching is: Issues · esphome/issues (github.com)
problem uploading esp8266 · Issue #1665 · esphome/issues (github.com)
Your issue is certainly strange.
From the console again, could you docker exec ab123 default gateway IP just to confirm that esphome can see other IPs and working correctly?
is that the correct command?
Forgot the ping.
Docker exec containername ping your_defaultgateway_ip
This will confirm whether esphome container can see your gateway on your network segment. Proves that esphome networking is working as planned.
Cool. That proves that esphome is communicating properly.
The compile/upload of the .bin file appears to be working.
If you reset the esp8266 device via reset button, can you monitor any serial logs?
Is the device pingable from another device on that vlan? Perhaps a PC/Mac/Pi?
Here is a bit of a long-shot, but I found some pointers here:
I saw that you were runing esp8285 board and it may have some frameworks that are newer. Some people are mentioning that is may be helpful for Ubiquiti networks (not sure if you have that).
board: esp8285
framework:
version: recommended
So the device I am using is one of the MagicLED wifi controllers (flux integration in HA I believe), and so it does not have a reset button (that I know of?) 
OOOOOHHHH If i change my laptop over to the same subnet as the device, I CAN PING it! So what the heck happened…why is my network all of a sudden not allowing cross subnet communication?
Oh, I think I have one of those controllers – I haven’t used it in a while as my wife didn’t care for LEDs above a cabinet in our bedroom. Congrats on flashing that badboy! Respect!
So, I think you have narrowed down to cross-subnet communications. Perhaps easy check (which I doubt has changed), but perhaps checking secrets.yaml to see if anything has changed on your gateways and subnets. I’m guessing they haven’t changed. However at least you are narrowing it down.
I’d be over my ski-tips guiding you on any vlan configurations, but I suspect that is what may be causing the cross-subnet communication issues.
I’ve read a little about 2.5mhz settings vs. 5mhz settings and IGMPv3 settings on Ubiquiti gear, etc, but I don’t have Ubiquiti gear in front of me to play with. My home has the consumer gear meaning no vlans (jealous).
Good luck on further troubleshooting. I’m sure you’ll get it. Let me know how things work out. I’m sure it is something small, yet so significant.
Hmm… so playing with it a little further, it only seems to be the ESPHome devices that I cannot ping unless I am on the same subnet. If I put any other device on that vlan, I can ping it just fine.
I have fixed it! It was due to an incorrect gateway in my ESPHome Secrets yaml. I had it as 192.168.10.1 (as that is what my router is), but it should be 192.168.20.1, as it is on vlan 20! Thank you so much for all of your help!
EDIT: ESPHome over VLAN became unreachable - #5 by Ronaldt helped me out as well!
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Yeah! Fantastic. I knew you’d find root cause. So glad that you got it working.