Spyke

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What to use as DHCP server?

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

  1. 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.

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Help with Port Forwarding (I think)

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.

piracy

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Is this the place for help with setting up Sonarr/Radarr?

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No worries.

To make your life easier you will want to pass the same "volume" to each of your containers so that they are all able to interact with the files the same way. For instance, if your movies are in /home/username/media/movies then make a volume for radarr, you can name it anything but for this example I'll use data, like so in docker:

/home/username/media:/data

Then inside radarr you can make your path inside.media management, root folders:

/data/movies

It works the same way for your downloads, just make sure your downloads go somewhere in the media folder, eg. /home//media/downloads. Then for your download client, use /home/username/media:/data in docker and inside the client download to /data/downloads.

Hope that makes sense

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Jellyfin, Caddy, and Cloudflare Real IP

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I have followed that guide which let me to a few GitHub issues.

Here is what I have put in my config:

servers {
        trusted_proxies cloudflare {
                        interval 12h
                        timeout 15s
                }
        trusted_proxies static private_ranges
        client_ip_headers Cf-Connecting-Ip X-Forwarded-For
        }
}

I have also added all Cloudflare IPs in Jellyfin's known proxies:

103.21.244.0/22, 103.22.200.0/22, 103.31.4.0/22, 104.16.0.0/13, 104.24.0.0/14, 108.162.192.0/18, 131.0.72.0/22, 141.101.64.0/18, 162.158.0.0/15, 172.64.0.0/13, 173.245.48.0/20, 188.114.96.0/20, 190.93.240.0/20, 197.234.240.0/22, 198.41.128.0/17

Yet, I'm still not seeing the real IPs.

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Amount of RJ45 Ports on Home Server?

Unless you're planning on virtualizing your router on the server (think OPNsense VM or something) then really only one ethernet port is required. Otherwise the sky is the limit. For example, mine has a 1 Gbps port, a 2.5gbps port, and two 10 Gbps ports.

Depends on what you want/need and whether you want to future proof I guess.