Mac OS X Terminal: -bash: $: command not found
Your PATH looks fine. The PATH variable is a collection of folders/directories in which the shell looks for commands to execute. So if you install additional software like MacGPG there might get new parts added.

But I assume that the command you are calling is called pagekite.py and not actually $. So you should call it like

pagekite.py --signup


or (if it is in your current folder/directory)

./pagekite.py --signup


The $ is often used in documentation to represent the shell command prompt and should not be entered to run the command afterwards.