Considering content manager is the worst transfer software for a major device out there, yes Media Go was more open. You can't even specify multiple folders for media with content manager.
Did the Media Go software have anything to do with the PSP piracy issues? I understand why Sony would be hesistant to offer a super open thing for games and game saves, but for media files I don't see the big deal. I don't use my Vita for media either because of these issues.
The Media Go software didn't really encourage piracy, but hackers were able to hack into consoles via standard USB ports. In addition, they can copy their warez into the console freely via the USB drive mechanism.
Vita's proprietary USB port probably introduces stricter I/O mechanisms (e.g., Not every program can copy files into Vita). The Vita Content Manager further checks with PSN to allow/reject executables entering the system. If this check is performed outside Vita, then it can be circumvented easily.
Yeah, I had a problem copying backgrounds cause I had a ton of images in my directory too. My suggestion is to not point the content manager at your real image/music directories but instead have separate Vita Image/Vita Music directories on your computer, then put only what you want to copy to the vita in those directories. It makes getting something on the vita a two step process, but it's generally easier than browsing everything from the vita's side.
Yeah, this is the basic idea. It should not be difficult for Sony to fix Content Manager:
(1) Make Content Manager import multiple files and directories. Keep this pre-defined list in a config file like what they do now.
(2) Change MediaGo. Instead of copying the files and folders into a USB drive directly, make MediaGo write the full path of the target files and folders into CMA's config file. Then add a "Sync" or "Start" button to kick the CMA so that it reads the new paths and starts the copy process automatically. The Vita Content Manager will still carrying out the same security checks for files entering Vita.
In general, the concept of using Vita to browse and control file sync/download is not wrong. In the post-PC era, some of us may not sync files to PC/Mac anymore. We may sync them to a cloud or an iPad instead. We may also do it wirelessly instead of via USB. So Sony will still need to improve the Content Manager navigating, categorizing and searching mechanisms even if we can side-step it with the MediaGo change above.
Hope Sony continue to improve both the Content Manager and the CMA integration with native sync software (e.g., iTunes, MediaGo).