As of September 25th 2019, my favorite software (besides from Simple DNS Plus and Simple Failover) is:
Software Development
Server software
Desktop software / Utilities
VirtualBox - https://www.virtualbox.org
Amazing virtual machine software for the desktop.
I prefer to use this over Hyper-V (which comes with Windows 10 Pro) because it is much easier to move virtual machines between host computers. I simply store the VM images on a portable harddisk and move this between host machines as needed. This is possible because VirtualBox (like VMWare Workstation) is a "level 2" hypervisor - meaning that hardware is virtualized. Hyper-V is "level 1" meaning that VMs interface directly with the hardware, and thus are much harder to move to a different host machine.
I used VMWare Workstation for man years, but VirtualBox does exactly the same, only for free.
KeePass Password Safe - http://keepass.info
Great (free) program for storing passwords.
Storing the (encrypted) password database on DropBox makes it easy to sync between computers and my (Android) phone.
CutePDF Professional - http://www.cutepdf.com
I mostly use it for scanning to PDF files, and for merging multiple PDF files into one.
TreeSize Free - https://www.jam-software.com/treesize_free
Figure out what is using all that hard disk space.
Macrium Reflect - http://www.macrium.com
Great software for cloning / migrating harddisks.
CloudBerry Backup - https://www.cloudberrylab.com/backup.aspx
For backing up PCs to the cloud. Using this with Amazon S3.
SyncBackPro - https://www.2brightsparks.com
For syncing local files and backing up to the cloud.
VeraCrypt - https://www.veracrypt.fr
For making an virtual encrypted harddisk - which lives in a file on your regular harddisk.
Better and cheaper than BitLocker - better because I don't have to encrypt the whole disk (which could cause others problems) and cheaper because it is free and BitLocker only comes with Windows 10 Pro.
This is where I keep source code / Git repositories on my laptop. If someone steals the laptop, at least this stuff is safe.
7-Zip - http://www.7-zip.org
Great for working with zip files and other compressed file archives.
I primarily use this because the built-in function for creating zip files in Windows 10 doesn't work with file names containing non-english characters.
Office 2013 - https://microsoft.com
I did have an Office 365 subscription for a number of years, but cancelled this in September 2019 and went back to Office 2013 (for which I own a perpetual license). I realized that I rarely use the Office programs anymore, and that nothing significant has been added since the 2013 version.
Photography / graphics / video
Photoshop CS5 - https://adobe.com
I did have an Adobe CC (Creative Cloud) subscription for a number of years, but cancelled this in september 2019, and went back to Photoshop CS5 (which I paid a lot of money for back when Adobe sold perpetual licenses). I realized that CS5 still does everything I need (and starts up a lost faster than the current Photoshop version), and as I was also replacing Lightroom with Capture One (see below), I really didn't need CC anymore.
Capture One - https://www.captureone.com
For RAW photo file processing and photo management.
Replaced Adobe Lightroom (Classic) with this in September 2019.
Adobe Premiere Elements - https://adobe.com
Nice program for basic video editing (clipping, merging, adding titles, etc.)
Web-apps
I have tried many different tools in all these categories over the years, and I can highly recommend all of the above over any competitors that I know of.
If you know of any better alternatives please do tell me in the comments below - always looking for better toys :-)