Great question!
Here's what I do to update my Windows TF2 Dedicated Server. I have a folder called "C:\STEAMCMD" that has all of my STEAMCMD files, including these two below:
I made a file called "update.bat" that contains this info:
PHP Code:
steamcmd +runscript tf2update.txt
I made a file called tf2update.txt that has this info:
PHP Code:
login anonymous
force_install_dir C:\TF2Server
app_update 232250 validate
quit
When I want to update, or validate an update, I go to a command prompt and type:
PHP Code:
cd\steamcmd
update
That's it.
I hope this helps.