The rubygem is a package installable using the rubygem package manager (you wont get any benefit from just downloading the files from github, unless you also use the gem tools to compile it in to a gem and install it.
To install the rubygem, make sure you have libusb 1.x and ruby 1.9.x or ruby 2.0 installed (mac's and many versions of linux come with 1.8 installed, which is no good for this), then open a terminal and run 'gem install digiusb'. You might need to sudo that depending on your platform. Finally, you aught to be able to just type 'digiterm' in your terminal window and it will find the most recently attached digispark, connect to it, and start outputting everything printed via DigiUSB on the device and forwarding keystrokes from the terminal window in to the digispark.
Because of all this complex interdependency, although in my view the digiterm is still the nicest digiusb monitor app, it's not a good option for beginners. I don't know much about the other alternatives. DigiKeyboard is certainly a great option because you don't need to install any special stuff. All of these are however kind of crummy, because the USB libraries require constant attention. DigiUSB is the most relaxed of the bunch (at least when using the rubygem), only requiring you refresh it once per second at minimum. Still, if you have long running loops digiusb is not a good option.
Digispark is able to be cheap because it eliminates the dedicated usb serial converter chip present on most arduinos, but that trade off is not without it's price. Still I fully expect print debugging to improve in the future. It is already so much better thanks to DigiKeyboard.print() being added.