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Software

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!