If you want it automated, an oversimplified way would be to use an MS-DOS batch file or a Unix equivalent for Mac OS or Linux. I could write one in 10 minutes. You'd still need a removable drive, though. The main problem is you would need to interact where an identical filename exists. Forgotten how (un)sophisticated each console is regarding mentioning which is newer.
Life is like an adventure game: if you don't click, you don't get it