A few comments:
I have successfully gotten both the DigiCDC (serial port) "echo" and DigiUSB "echo" examples to work with the DigiSpark Pro on a Mac running OSX 10.9 (Mavericks).
Of note:
1) I needed to install Xcode and its command line tools, then install the homebrew package manager, then "brew install libusb libusb-compat"
2) I've used both the Arduino 1.5.8 (as well as built the 1.6.x from source)
2) I used the "Digistump1.5Addons-v09Mac.zip package and put the "hardware" folder in ~/Documents/Arduino/ per the instructions.
3) The DigiCDC app compiled without complaint. I hit the "upload" button, then plugged the device into a USB 2.0 hub plugged into my iMac. I could then see the device appear on the Arduino Tools -> Port menu as both /dev/tty.usbmodem141111 and as /dev/cu.usbmodem141111 Connecting as the tty device, I could type a line of characters, hit "send" and see them echo back to me.
4) The DigiUSB examples needed some editing:
I needed to add a "const" before several of the arrays in ~/Documents/Arduino/hardware/avr/libraries/DigiUSB/usbdrv.c so that the declaration in usbdrv.h matched what was in usbdrv.c, e.g. changing "PROGMEM char usbDescriptorString0[] " to "PROGMEM const char usbDescriptorString0[]", etc. The error messages in the IDE at compile time give you the line numbers to change.
I also needed to comment out the following lines in ~/Documents/Arduino/hardware/avr/libraries/DigiUSB/DigiUSB.cpp
#if F_CPU != 16500000L
#error "You must use Digispark (Tiny Core) board to use USB libraries"
#endif
Those lines were a holdover from the original DigiSpark.
On the Mac side, the DigiUSB device is not immediately visible. There was an old program provided in the DigisparkArduino-MacOSX-1.0.4-May19 package under DigiUSB Programs/source/monitor called digiusb.cpp. Using the current libusb-compat installed by homebrew I can build it with:
g++ -I/usr/local/Cellar/libusb-compat/0.1.5/include /usr/local/lib/libusb-0.1.4.dylib -lncurses -O -g -D MAC_OS -D_DARWIN_USE_64_BIT_INODE=1 -o digiusb digiusb.cpp
The text of digiusb.cpp on the host side is at:
http://sourceforge.net/projects/digistump/files/DigisparkArduino-MacOSX-1.0.4-May19.zipin DigiUSB Programs/source/monitor/digiusb.cpp
This builds and runs, and also does simple character echo back to the screen what I type (and hit return) for.
The other DigiUSB-based examples require similar minor patching to run with the current gcc-avr compiler included in Arduino.
I hope this is of some help to the other folks here who were commenting about difficulties getting the examples to run.