Well, this response is pretty late, but your problem is definitely solvable. Even in 64 bit mode.
I bought a Roland PC-300 ED on eBay yesterday, and had the same issue, but a quick driver hack sorted it out. We can't resonably expect manufacturers to maintain drivers for legacy products. We have to get off our arse and do it ourselves. Huge thanks to Yves Salathe (https://github.com/ysalathe/GenericUSBMIDI) for doing exactly that!
DON'T follow the Roland advice about making 2 extra devices in Audio MIDI window. It won't hurt anything but it's unnecessary.
Grab https://www.dropbox.com/sh/oonzuhyk9nul7ny/AABd_aszy457kCQY07WP8Mu_a?dl=0 from my dropbox, place it in your MacHD-Library-Audio-MIDI Drivers folder, and reboot.
You should find the PC-300 in the MIDI setup window after this, if it's plugged in and turned on when rebooting. (Power switch on USB and other switch on PC)
I actually had a driver conflict and had to move the other plugins out of that folder and re-add them one by one to figure out which was conflicting. When I first rebooted with no other driver plugin in the folder my Audio/MIDI window showed the PC-300 - if required you can rescan MIDI devices in that window too to see if that'll bring it up.
Don't put the plugin in your User Library folder - use the whole machine Library folder on your MacHD.
Working fine for me today with Mavericks 10.9.5 on MacBook Pro late 2013. Power and MIDI data all flowing over the USB cable.
Cheers
Neil