Base software to install on windows servers

Latest version of powershell and powershell ISE
http://windirstat.info/ - Disk usage report
http://www.7-zip.org/ - Opens lots of archives
http://www.wireshark.org/ - Network traffic capture
http://technet.microsoft.com/en-us/sysinternals/bb842062 - Sysinternals Suite lots of very useful tools
http://technet.microsoft.com/en-us/library/cc771275(v=ws.10).aspx - Telnet client
Your backup or monitoring agent if required
Your AV solution
Configure NTP
Configure Logging
Right click -> Computer -> Properties -> Advanced -> Startup and Recovery -> Settings -> Kernel memory dump

http://getgreenshot.org/ - screenshots

http://www.nirsoft.net/ - suite of tools bluescreen view being popular

RSAT - remote admin tools for windows server etc (install and then appwiz to add them)
ASDM - for Cisco
filezilla - transfering files
foxit reader - PDF
google chrome - web browser
java - required for asdm and maybe other aps
mRemoteNG - saving connections, ssh rdp, vnc, webpage external app
remote desktop connection manager (might not be needed if you have above)
keepass - password store
zenmap - gui for nmap

portqueryui - good for checking open ports and a nice screenshot

openssl (sclient) W32openssl

openssl s_client -connect www.google.com:443

openssl can convert certs too

sublime text or notepad++
sublimetext editor
winscp
grep for windows
dig for windows
my traceroute (https://winmtr.en.uptodown.com/windows)

sysinternals suite 

maybe microsoft powertoys for admins

psexec can be replaced by powershell PSSessions or Invoke-command. Psexec is still great because it runs locally on the target system. Can run as local system account.

NTRadping - Radius testing
https://community.microfocus.com/t5/OES-Tips-Information/NTRadPing-1-5-RADIUS-Test-Utility/ta-p/1777768