Need Help with Setting up Remote Access

Hello everybody,

I’m new here and recently started the adventure into home automation. So far, I have two aeotec bulbs connected to my RPI 3 HA instance - along with ecobee 3 lite WiFi thermostat connected to it.

I’ve been trying to setup remote access so it can be accessed from outside of my home network. With that said, I have attempted the process for setting up remote access -> duckdns -> create a dns -> vi -> etc. and onto let encrypt. I can’t get lets encrypt to do its thing. It either returns a connection timed out. I did play with port forwarding on my router; which gave me some other errors (max retries port 443/ something along those lines).

Currently, I have a netgear wnr2000v3 with dd-wrt running on it with rules to port forward 80 and 443; as well as 8123. The raspberry pi does not have a static ip at the moment - I suspect that might help, but once I did that it seemed to break the ecobee functionality in the iOS app. Any and all help is appreciated.