This section is going to be a little bit limited now since most software/stuff I get for my modern machines is downloaded online. I'm also not bothering to categorize because I only use a HANDFUL of applications, and try to stay open source and cheap-as-free as possible.
Link Title] O/S Description
Microsoft Windows 10 Windows I still use Microsoft Windows for SOME of the things I do, though I'm slowly moving away from it at home. Honestly, if you're running anything other than a Macintosh, you might be better off using this if you're not up to speed on *nix operating systems. After all, it is the most popular operating system in the world, and while their support forms feature some people who I question their "SME" (Subject Matter Expert) status, it still is a pretty decent operating system, even if life with it can be a roller coaster. Just keep it updated and stay on Windows UPdate and your OEM's driver updates like they are your two spoiled and moody teenage kids and you'll do just fine.
Linux Mint Linux This is currently my top operating system of choice, and I prefer it for a few good reasons. First off, the interface should be familiar enough to any Windows user to pick up on fairly quickly. Secondly, it does have a pretty good software portal that can take additional repositories into consideration allowing for easy (and proper) installation of software by novices. Another nice thing is for a multi-platform, O/S agnostic like myself, I can run most things from any platform on Linux including: Vintage Windows (VM/Wine), Vintage DOS (VM/DOSBox), Vintage Mac (MiniVMac, BasiliskII), modern Mac (VM), Linux (native), Modern Windows (Wine/VM), Android (there's a pretty good android emulator I hear) - plus I can run console games in Linux like Atari 2600, NES, SNES, Game Boy, probably up to Wii with today's hardware levels.
Mac OSX Apple I have an iMac, and I quite well like Mac OS/X, and it is a *nix variant so a "power user" like myself can probably do everything I can do with LInux on it (and more actually, being as I'm a musician, I use it mostly for Garage Band). For your Macintosh, to pick the correct O/S, either visit the site above for a vintage mac, or for a modern Mac (iMac/MacBook starting about 2010 methinks), you can use Command+Option+R at boot time to restore and use the internet to download the latest O/S release that your mac supports. The link is just a support page to help locate what to do and what works on what mac.
Mozilla Firefox Windows, Android, iOS, OS/X, *.nix Mozilla Firefox is still my browser of choice. While I'm not too happy about them removing FTP Support from it (see below), I am happy that they are at least still around as I'm not too fond of Chrome/Edge, and I like having all these add-ins I can use to control and reign in advertising, unwanted scripts, and other stuff. Yeah Zoomers, I get that the internet is run on "advertising", but does nobody release not a single intelligent person ever bought a product because of an internet ad?
FileZilla Windows, iOS, OS/X, *.nix I currently use FileZilla for viewing FTP Servers and doing FTP transfers to my vintage machines using mTCP. The reason I took to using this is primarily for the last reason, though now I do so from the other side of things due to Mozilla taking FTP out of it's software stack.
WinRAR Windows, Android, iOS, OS/X, *.nix For my modern systems in dealing with archives, I use WinRAR. I prefer WinRAR because I don't need to buy it to use the right click "extract here" option, which is all I ever really use it for. And it opens darn near everything from day one of the IBM PC so that's a good way for me to manage my archives for my vintage PCs as well on a modern