Out of curiousity, any reason why I can't just get the X windows to pop up on the jump server? like whats the technical limitation im running into?
Windows doesn't have an X Server installed by default.
Here's what happening.
1) ssh session is established with X11 forwarding enabled.
2) GUI program is started.
3) GUI program starts sending GUI data over the ssh connection to be received by the X server on the local computer.
4) X Server renders the GUI elements with all the processing happening on the server.
You don't have an X Server, so step 4 never happens, and possibly, step 3 doesn't happen if you don't specify X11 forwarding in PuTTY.
Try MobaXterm. You don't have to install anything, and the X Windows environment is already setup. You should be able to issue "ssh username@server" then "xterm &" with everything just working. I haven't used MobaXterm in a while, since I got a dedicated Linux box at work, but that's the way it used to work, if I remember correctly. If that doesn't work, you may need to issue "ssh -X username@server" to get the tunneling working.