1- Retry 0: Got TIMEOUT when trying to connect using the Intel Arduino IDE
One solution:
log in via SSH, or serial, and delete or rename /sketch/sketch.elf file, and then reboot, or at minimum kill the existing running sketch.elf process. Its particularly an issue with porting over a simple Arduino example, or running the AnalogReadSerial, or DigitalReadSerial examples from the IDE. The Intel IoT platforms share the USB connection with the Serial Monitor, unlike a standard Arduino.
Another solution:
This is for OSX specifically, Windows may have a similar issue if you are accidentally using the wrong COM port.
If you are using Intel Arduino IDE with either Intel Galileo or Intel Edison and you are getting the following error: Retry 0: Got TIMEOUT – it is likely that your IDE has automatically selected the wrong serial port by default.
Click Tools -> Serial Port -> /dev/cu.usbmodemXXXX. There may be several, try a couple of them with the Blink sketch to find the proper one.
Note: Don’t try to use the serial port with naming convention /dev/cu.usbmodel-XXXXXXX (8 characters and a dash). This may also help for Retry 0: Timeout on pathname and Transfer Incomplete. This error may occur if you plug in two Micro-USB cables into the Arduino breakout board. The first cable (when plugged into the middle micro-USB port) will reveal a number of ports specifically for use with Arduino. If you plug in a second cable, you will get two more which are useful for getting terminal access to Edison but will confuse Arduino IDE.
2- Unable to deploy code using with the Arduino IDE in Windows
3- Failed to initialise Arduino board TriState
If you are getting "Intel Edison Failed to initialise Arduino board TriState, check i2c devices! FATAL," your copy of libMRAA is out of date or simply not installed.
Run the following commands:
For more such intel IoT resources and tools from Intel, please visit the Intel® Developer Zone
Source: https://software.intel.com/en-us/articles/arduino-for-intel-iot-platforms-troubleshooting-and-faq