Having spent many hundreds of hours on EAGLE, it's my go-to now. I can't attest to any of the functionality of KiCAD, but if it's the right style for you then go for it. Freeware EAGLE is fine for smaller 2-layer boards and has a tonne of parts that I haven't yet encountered errors on. You really have to go deep into making new packages though, and the interface and workflow leaves something to be desired. Once that learning curve is crossed it makes a lot more sense. For larger PCBs you need to think about one of the paid versions. I wish there was an intermediate pricing between the hobby and pro versions, but such is life.
Normally when I design things for MIDIbox I have the related schematics open on browser tabs. This way I try to maintain pin compatibility and functionality with the existing hardware whenever possible.
On the subject of "where are the PCB designs?" I'm currently in two minds about this. People who haven't gone through the process generally don't have a grasp of the time, energy and cost involved. Not only learning about (and perhaps paying for) the software, but all the research that goes into good design and getting the circuit to function, which after meticulous planning often requires a few board revisions. By no means am I accusing anyone here of having bad intentions, but I've seen numerous examples of people taking advantage of others' goodwill.
The MIDIbox SID has been a source of controversy in the past, with many unauthorised clones being built and sold. Also take a look at Mutable Instruments, where Olivier Gillet graciously shares all software and hardware under CC-by-SA. Some smell an opportunity and simply upload the gerbers to make a tidy resale profit for the minimal effort of a few emails and distributed shipping. The accessibility of professional PCBs has increased dramatically, mostly due to batching services that mean you can order as few as five (or less) at a time. IMO (and perhaps I'm a bit cynical) is that many of the people asking for design files have no intention of making derivative works (i.e. improvements in the sense of Creative Commons), but simply want the lower cost boards from China. As a designer and builder, I'd much prefer if people bought things via me as a means of supporting my work. With an online repository of design files, there's no separating the good and bad intentions.
In saying that, how do you put a value on the incredible software developed by (mostly) TK. and provided freely? Is it right for me to withhold designs for hardware I've tailored to his software projects, schematic fundamentals like SRIO chains etc., or prototype concepts like the MBProgramma of Hawkeye/jojjelito? I think that if I definitely knew I wouldn't have to rely on sales of hardware in this strange world where work isn't guaranteed -- and also that people had genuine intent to learn and improve upon others' work rather than taking the cheapest route to the bottom -- I would certainly be more comfortable with fully open sourced hardware. I'm still working on the answer to that :).
Sorry for the rant, and best of luck with KiCAD!