Might be his problem. but still it can take a long time to send 4 gigs. My sd card is 32 gigs and its a fast one... even at that its time consuming when your talking about 4+ gigs!
About pdf s, the sony can handle just fine. Personally dont even bother converting them anymore. Satisfied with the reflowable text... but it has some caveats... nothing is perfect i guess
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If you really need to convert i started using solid pdf converter, and it does a nice job. Again its not perfect but its the closest i ve come!