Software that I find useful but which is something a PITA to configure. Or, I just don't use it very often and sometimes forget about it.

• Atom - sometimes a pain but free, extremely flexible, and does really good regex.
• AutoHotKey - the one thing that makes Window bearable (this and StrokePlus.net)
• Edge - The M$ browser
• Firefox
• Google
• dig & host - better dns lookups
• Nmap & Zenmap
• Office - A steaming pile that everyone uses because they're not curious enough to go see if there's something better out there. There is.
• OpenSSL
• Password Management - Various tools for managing passwords.
• SecureCRT
• StrokesPlus.net - the one feature that I can't duplicate on Mac
• tcpdump - Capture filters!