Can the EPSON WorkForce DS-5000 scan transparencies?

Yes that shouldn't be a problem, I'm assuming by transparencies you mean things like the clear film that people print on for overhead projectors and tracing paper.

What is the maximum document size that the EPSON WorkForce DS-50000 scanner can handle?

The maximum document size that the EPSON WorkForce DS-50000 scanner can handle is 11.7 inches x 17 inches.

Questions & Answers: EPSON WorkForce DS 50000 Scanner - Newegg.com

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Epson America
Item#: N82E16838110047
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EPSON WorkForce DS-50000 (B11B204121) CCD 600 x 600 dpi Photo Document Scanner

11x17in. flatbed scanning surface for full-sized, larger scans
600 dpi max resolution output for document and image clarity
Scan to cloud options for quick archiving and sharing
Hi-Speed, 2.0 USB connectivity offers fast data transfer
Works well in offices with mixed operating system equipment

$2,039^.00 –