Here are a couple of suggestions. Based on your description, your issues are between MACOS and tinyG for now and you have CoolTerm installed. You need to resolve the usb port connectivity issue before moving on to CP.
I cannot help directly with MACOS specifics, I run on Linux, so will speak Linux and expect you to translate to MACOS dialect. I know MACOS has its roots in Unix so is similar, but unique in detailed ways I am not familiar with.
Step one is to get MACOS properly accepting a connection from tinyG.
Here is what I would do in Linux space:
1. disconnect tinyG's USB from MAC
2. Reboot MAC
3. With a GUI file manager, navigate to /dev and click the GUI to sort the display of devices under /dev by date, decending order, most recent on top.
4. The most recent, and probably everything, will have a date field that is same as the boot time.
5. Without connecting tinyG yet, power it up and wait for the flashing LED to stop flashing (boot is complete). Hit the reset button, it will reboot(this is probably redundant, but ensures a clean boot, free of power up induced glitches, should they exist).
6. TinyG still not connected, refresh your file manager GUI.
7. Now insert tinyG's USB into the MAC, then refresh you GUI again (or it may auto-refresh).
8. You should see a new device appear under /dev, with connect time the insertion of the tinyG USB cable.
9. If there is no change in the /dev/ device list, you likely have an ftdi driver install issue. Devices appear as /dev/ttyUSB0 (Linux speak, not MAC) only after USB insertion detection and proper driver startup.
10. Open a command line console window in you GUI. In Linux, a 'dmesg' command will dump a long stream of messages, the most recent of which should be related to the USB insertion. In this file (URL) you will see the results of the dmesg command on my Linux machine, The top three lines are a disconnect event, the balance are the messages issued by the USB services after re-insertion, loading and starting up the driver.
https://dl.dropboxusercontent.com/u/50261731/dmesgtinyG.txt
11. If you do not see a new device appear in /dev, still check the output of 'dmesg' command. If the new USB device insertion was seen by MACOS, you will then likely see some error messages related to install driver failure for the new USB device. If there is nothing in the 'dmesg' report, perhaps try a different USB cable? It would not be the first time the cable turned defective in one of these adventures.
12. If MACos does not support 'dmesg' from the command line, look with an editor at the bottom of the system messages file. In Linux, from CLI, that would be 'cat /var/log/messages | tail', outputting USB related messages similar to dmesg above (tail by default prints only bottom 20 lines)
See if any of this produces useful information.
Hopefully someone who is more familiar with you version of MACos will stop by and more precisely speak your language.
AND, when you are finally getting a usable tinyG USB connection, get CoolTerm working again as it is somewhat simpler than Chhilipeppr.
Then move on to Chilipeppr again. What version of the serial-port-json-server do you have installed? Version 1.77 is the latest.
FINALLY, know that I will then recommend you update your tinyG FW to build 438.02. Build 380.08 is rather dated, will get you going with CoolTerm and probably Chilipeppr, but Chillipeppr works best with enhanced tinyG status messaging that is in 438.02 FW (and beyond).