Cory sitting down using a Lenovo X200 laptop Cory Rash wordmark / pixel art

Distributions:

I prefer freedom first, stability second.
Trisquel
Has been my go-to for years. It's always old and outdated, but extremely stable and reliable. If there's software I need that isn't available I can either build it from source or grab it through Guix.
Devuan
Debian without the SystemD and only using liberated media. I tried to use Gnuinos, which is the 100% FOSS version of Devuan, but it always breaks for me.
Debian
It just works. I prefer the other two, but Debian is the one I use on my web server.
ZorinOS
The distribution I recommend to newcomers. I don't use it myself (I have before and it's nearly identical to Windows), but if you're looking to get into GNU/Linux then this is the one to start with.

Desktop Environment:

I've tried to live in terminal based DE's, but as a designer they're just not for me or my workflow.
XFCE
My default. Simple, fast, lightweight, customizable, and all you'll ever need.
Gnome
Resource intensive, but it actually looks nice. I will always pick Gnome over KDE if forced to pick between the two.
JWM
If I'm using ancient hardware I prefer to use JWM for speed.

Software:

GNU Nano
Sue me. It's my favorite terminal based text editor. I also use vim, but nano is my default and go-to.
Mousepad
Similar to Microsoft Notepad and also Gedit. If I'm using a GUI, this is probably what I'm using.
KeePassXC
The only password manager you'll ever need. Supports OTP and password generation. Can be synchronized across all of your devices using something like Nextcloud or Syncthing.
NextCloud
The FOSS replacement for Dropbox. You need to self-host the server portion unless you're paying a third party to do it for you.
LibreOffice
Get away from Google Docs and Microsoft Word/Excel. LibreOffice and The Open Document Foundation are constantly fighting to keep basic document manipulation available to everyone.
Blender
If you're messing with 3D, this is a must.
InkScape
Currently the best 2D vector editing software on GNU/Linux. It even supports embroidery plug-ins.

Self Hosted:

Yunohost
A very handy all-in-one package to help you manage self hosting. Makes it very easy to get up and going with basic security pre-configured and minimal effort.
FreedomBox
Similar to Yunohost, but less services are supported.
Peertube
Host your own alternative to YouTube.
NextCloud
The FOSS Dropbox replacement.
Jellyfin
Get rid of Plex and migrate to Jellyfin for hosting all of your media content.

Android:

iodeOS
Currently the best ROM if your intention is using Android. It's basically LineageOS, but de-Googled. iodeOS promotes free software replacements for Google (microG) unlike GrapheneOS which installs the actual Google APKs on your phone and has their community on Discord.
LineageOS (Official)
The next best ROM after iode if your device isn't supported. I wouldn't trust third party sources and would only use official LineageOS supported devices.
F-Droid
An absolute must. This is the best place to get your software from.
Monocles Chat
This is just a fork of the excellent Conversations XMPP app but with support for more features like sending stickers, animated gifs, and a true black OLED theme.
Conversations
If you don't need the extra features then just go with the original. It has a long history of developer support and will likely continue to be developed for many years. XMPP as a protocol is very reliable and supports encryption. It's also much less bloated and faster than Matrix based chat apps like Element.