If I need to open a new thread for this, I'll be happy to. After installing DNS-crypt proxy and configuring pi-hole to use 127.0.0.1:5353 as upstream DNS, I'm getting the following:
$ dig pi-hole.net @127.0.0.1 -p 5353
; <<>> DiG 9.16.1-Ubuntu <<>> pi-hole.net @127.0.0.1 -p 5353
;; global options: +cmd
;; connection timed out; no servers could be reached
jorg@elder-mac-smash:~$ netstat -ano | grep 5353
udp 0 0 0.0.0.0:5353 0.0.0.0:* off (0.00/0/0)
udp6 0 0 :::5353 :::* off (0.00/0/0)
jorg@elder-mac-smash:~$
$ sudo service dnscrypt-proxy status
● dnscrypt-proxy.service - Encrypted/authenticated DNS proxy
Loaded: loaded (/etc/systemd/system/dnscrypt-proxy.service; enabled; vendor preset: enabled)
Active: activating (auto-restart) (Result: exit-code) since Wed 2020-07-22 18:27:21 UTC; 1s ago
Process: 344367 ExecStart=/opt/dnscrypt-proxy/dnscrypt-proxy -config dnscrypt-proxy.toml (code=exited, status=255/EXCEPTION)
Main PID: 344367 (code=exited, status=255/EXCEPTION)
I tried skimming through the dnscrypt-proxy.toml file and I didn't see anything there that looked off. I used the example-dnscrypt-proxy.toml file during setup. I followed this guide: GitHub - pi-hole/pi-hole: A black hole for Internet advertisements
Thanks to all!