Okay, I worked on this for a couple hours today and here's what I found:
Sometimes a com port might get into a state where scratchx can't open it. This apparently happened to the original poster as well as myself. This may be related to recent changes either in chrome or over at the scratchx website, I'm not sure.
The solution, which works on the version of Vorpal Scratch currently online (i.e. I did not have to change it) is pretty simple:
NOTE: These steps are for windows. I will be looking into whether this even happens on mac later today.
1) Make sure you have an internet connection (so drivers can download if needed) and turn on your computer volume (so you can hear the little doot doot doot sounds when devices are installed or removed).
2) Open device manager (just type "device manager" in the windows search bar and you'll find it)
3) Scroll down until you see the item "Ports (COM and LPT) and expand that to see all the com ports.
4) Plug in the gamepad. You should hear the doot doot doot sound and a new COM port should appear.
4) Find the COM port associated with the gamepad. If you're not sure which one it is, unplug the gamepad to see which one dissappears, then plug it back in again and note which new one appears.
5) right click on the com port associated with the gamepad and select UNINSTALL DEVICE. Wait for the com port to dissapear out of the list.
6) Unplug the gamepad. Wait a few seconds. Plug it in again. Wait for windows to reinstall the driver for the arduino nano, usually takes about 30 seconds.
This completely cleared up the issue for me. At first I thought some of my coding changes fixed it, but then I tried using the online version (which has not changed) and it worked there too. I was able to plug, unplug, replug in a different usb port, use the RESET CONNECTION block, over and over again, and it connected 100% of the time and started controlling the robot.
Please let me know if this fixes the problem for you, and I will then document this over on the wiki under the scratch section.
-Steve P.