I need to "more easily" enter a timestamp into various applications
that don't offer this functionality (i.e notepad, Outlook Task,
Calendar, Notes, etc).

Here's what I have that puts the time and date into clipboard:
//
Public Sub Main()
Dim TheDate As String = Date.Now.ToString
Clipboard.SetDataObject(TheDate, True)
End Sub
//

With this I can run the program from a shortcut, place the cursor
where I want to enter the timedate stamp and CTRL-V to paste it in.

Question: How can I enhance this programatically to identify the
active window (i.e. an Outlook Task Comment area) and have the program
automatically paste the time/date whereever the cursor is?

I wouldn't recommend using the Clipboard to transfer data between applications. 

You can identify the foreground active window by calling the API
function GetForegroundWindow and you can use the message WM_GETTEXT to
get its name.

Then when you need to write the current date/time in that window,
emulate the keyboard keys by using the .NET class
System.Windows.Forms.SendKeys. Use the function SendKeys.Send() to
send the date/time string to the active application.

~Hani

In Notepad you can get a timestamp by pressing F5.

Thanks Hani, while trying to figure things out (I'm a real novice at
VB.NET), I saw references to your point of not using clipboard, but
could not figure out the actual coding structure to make
GetForegroundWindow and WM_GETTEXT work properly - kept getting
compile errors.

Thanks willcodeforfood, didn't know that about Notepad - regretably,
my need for this utility is primarily focused on Outlook which doesn't
have that ability.