To the best of my knowledge (and anyone feel free to jump in and tell me differently!), if you’re installing E10 and using SSRS reports for your barcoding then you only have to install the font file on the SSRS server… but you also have to “install” the font into the Windows Font functionality (meaning copying the DWBAR39.TTF file into the Font folder, right-clicking it, and selecting Install Font… and then rebooting your server). If you are using Bartender to handle your barcoding, then you’ll need to install the font file on every PC that will be printing barcodes and also installing the Windows Font functionality on that PC as well.
Also to my knowledge, there isn’t an easy “mass” way to install fonts (if there is one at all).