Office 365 Migration Gotcha’s

Cant load One-Drive Sync tool to Windows Server for Small Business – read system requirements

There are far fewer blocked file types – way less blocked types than On-premises

Upload can handle numerous files, and a corpus way bigger than 2 GB, but long file names and file sizes for one file 2 GB or greater are still boundaries. – ​ – (scroll down to upload large files or many files to a document library)


So if running SBS you could migrate to SBS 2011 and then to 2012 Essentials and finally to 2012 R2 Standard, and use one drive sync tool or you could copy the files to usb, place on Windows 8 and use sync,

either way, make sure to do data analysis for large files and file types and consider the max_path depth when creating sharepoint libraries for copy locations