Another distro doesn’t magically fix difficulty for a custom setup. You can checkout other distros and see if maybe you like how they are laid out and how their package managers work, but the general config portion of deploying your apps is going to be the same regardless. Something to consider is how are you getting help for your setup? Is it some content creator you follow who generally does their videos/guides on ubuntu so that is how you figured everything out? Do you have friends or family who use it? If your source of knowledge and help is familiar with ubuntu, it is best to stick with it so you continue to have that resource. I can fumble around most distros, but if you want specific help, you are much better off asking me about specific issues inside an RPM based distro. I imagine others are similar in that they have generally applicable knowledge and a huge amount of specific distro knowledge since that is generally what they use.

Personally, I think Ubuntu is the most friendly distribution when you’re starting out, just because there are many tutorials written for it. I also think more things work out-of-the-box than on RedHat-based distributions.

I run Debian for all my homelab servers: stable, fast, (community) support, and secure.

I go the Debian route as I find it much less bloated than Ubuntu, which I started out with when I moved to Linux. When I say bloated I mean extra packages I feel are not needed, not annoying or junk packages like that. Ubuntu is pretty good about reviewing packages before including them in the base install. I like installing just the packages required.

I run my Nextcloud instance in a Docker container on my file server.

Agreed with others on here about Ubuntu. I have one server that I threw a bunch of stuff on and spent many hours messing with the nginx configuration file before everything was working correctly (Nextcloud, another website, and a VoIP thing). Changing the OS won’t make it any easier since the biggest hurdle is getting the configs right…

I like Alpine Linux for my VPS servers, but that’s because it’s very lightweight, not because of ease of use.

For user friendliness I’ve heard really good things about Yunohost, which runs on Debian and lets you manage a lot of different software, Nextcloud included

Server 1: Gigabyte BRIX w/ Debian 11

• Home Assistant

Server 2: Asus Mini Desktop w/ Ubuntu 22.04 Docker:

• Portainer
• PiHole
• Roundcube
• Monica
• Nextcloud
• Dozzle
• Bitwarden
• Tandoor Recipes
• Log Analyzer
• Plex
• Ombi
• Prowlarr
• Radarr
• Sonarr
• Readarr
• Lidarr
• SABNzbd

Native:

• GlusterFS
• Fail2Ban
• iPerf3 Server
• Keepalived (AWS hot standby for some services)

For Nextcloud I would choose something which has snaps and here the Ubuntu is the original snaps one. I would do that because the snop for Nextcloud is amazing. I’ve been running it for a couple of years now and it updates itself always without any problems, it’s that good.

Especially if you’re not so skilled at administrating then Ubuntu is nice because all the how-to’s are written for it.

I use Yunohost, so you start with a Debian install and run their script. YNH makes self hosting very convenient.

Specific to your proxy issue, I’d highly recommend nginx proxy manager, it’s a gui for nginx and helped me with a lot of issues getting other proxies to work initially. I still use it a couple years in simply for the ease of use

If you can do everything with Docker/Docker Compose, you free yourself from worrying about the underlying system. Docker becomes what you need to learn, and the worst part of a Linux setup is just getting Docker installed and updated.

Ubuntu would be my Linux pick, though. Long support, paid support if necessary, and a very large community.

I saw that something like Ansible-NAS might be an easy and safe Solution?