You will need to run a reverse proxy on one of your VMs ( I use Caddy, it’s very simple), and forward port 80/443 to your reverse proxy.

Within your reverse proxy, you can tell it what port corresponds to which address and it will send you to the right service.

This is obviously an oversimplified answer, but there are many Caddy guides and I can help you with any specific questions.

Try using the local IP of the machine instead of localhost.

Your config looks good to me. I’m thinking you may have a permissions error with your media store folder. What permissions do you have set for it?

That’s very normal regarding the crash trying to join #matrix:matrix.org. You need much higher specs and need to be using Postgres database, MySQL probably won’t handle it.

Can you post a sanitized version of your homeserver.yaml so we can take a look at your config?

Also are you running docker or something else?

Thanks, didn’t notice that. I edited my comment to reflect.

To me it sounds like you don’t have a DHCP problem at all, the issue is no website can be resolved when your DNS is down (PiHole).

You really have two options:

1. Make sure the PiHole stays up 24/7, with minor downtime for maybe a reboot or an update.

or

2. Setup an additional raspberrypi with PiHole and use gravity-sync to keep them synced. Then, I would run ISC-DHCP server on both the raspberrypi’s, one as the primary and the other as the secondary. That way you can specify both of your DNS servers. Make them authoritative and disable your routers DHCP. You can take a look at this guide:

https://stevendiver.com/2020/02/21/isc-dhcp-failover-configuration/

Personally, I like to keep the wife happy so I have option 2 at home, that way the internet never goes down when I tinker.

Edit: Didn’t notice you said your router can’t issue out two DNS servers. I’ve never heard of that.