The worst part about the tools is licensing. That is such a pain in the butt. MSDN (visual studio subscription I think is the new name) is a GREAT example (as is office 365). The license/subscription is licensed to the individual if I read the docs right. As such, if I install an MSDN version of a tool on my WORK machine, all users who can log into that machine need to have an MSDN license. To install an MSDN tool on a machine, you need an MSDN license. Same thing with Office 365. At my workplace, I got an O365 license before IT did. IT was not licensed to install it on my computer, so they just provided me the link and I did it myself.
Now on the other hand, O365 is licensed to me and I can have it installed on up to 5 machines that I use. It is tied to my Microsoft account and NOT to my physical computer. So I can use my work purchased Office for personal stuff on my personal laptop as long as I don't exceed the 5 machine limit.
but as for tools that I use regularly, SQL Prompt, SSMS (2008 through 18), visual studio pro, notepad++, gitlab, git, remote desktop manager free, sql monitor, jira, database health monitor. Now tools that help me work that are not exactly work related - equalizer APO, OBS Studio, Stereo Tool. There is something to be said about listening to music while you work that just sounds right in your headphones and having equalizer APO and Stereo tool (both free, but I recommend paying for stereo tool to remove the trial "beeps").