Upload to YouTube for the captions, then youtube-dl to a VLC playlist or something? (Or to be a bit more pro, snag the captions from the download and remix them into the original source.)
Yeah...I may just suck it up and create the captions myself, put the videos on USB and play it through USB. We don't need to mess with YouTube and we can cancel the Youtube Red account, and be 100% accurate on the closed captions. That was my ultimate solution, just need to find the time.