Is it possible that crashing could indicate a bug rather than an intentional limit? Examining the log files might help shed light on this. IIRC, Mac OS X has a Log File Viewer, in the Utilities sub-folder of Applications. Also, Apple's forums often have posts about things like this.
Google Drive as advertised as not having a limit on file size but when I try to sync a 6GB+ Virtualbox file in crashes in OS X. I was thinking I could sync an Ubuntu VM since I have unlimited bandwidth at 100 Mbs upload/download
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