I have 2 ideas.
=== route #1 ===
Does this “to Synology” mean… to Synology management (DSM) port, or to the port of the reverse proxy server on Synology?
Could you share the setup screen in pi-hole?
Is this “port” the port for pi-hole, or the port for nas?
Could you show us your reverse proxy setup screen from Synology?
If you setup another reverse proxy of nas.mydomain.com:443 https, to http://192.168.1.153:(your DSM port), would that work when you access from outside?
It’s fine. For a reverse proxy setup, you could point that to http://192.168.1.154:8123, no ssl cert is needed.
This statement need to be checked. When you do use that ha.mydomain.com from LAN, it goes to pihole for dns lookup, and then with the local dns rule you set, you’d go directly to 192.168.1.154. This does not go through reverse proxy.
=== route #2 ===
I am actually thinking about the same thing.
Given you have HAOS, and you and do add-ons easily, then you can look into this add-on:
New Add-On: Cloudflared - Share your Projects! - Home Assistant Community (home-assistant.io)
I setup mine in 30 minutes. Including the time to register my account and domain name.
And the best part is that you don’t even need to open any port on your router.