Rekordbox emergency loops & playlist issues

Hi guys,

Not sure what my luck is with rekordbox but every time I try to use my playlists on a player, something or the other happens, let me break it down:

-The first ever time I used rekordbox in 2015, suddenly my tracks started going into an emergency loop and it was impossible to play.

-The second time I exported the files to a usb, nothing popped up, ie the CDJ did not even detect the pen drive.

-Recently, the exporting completed but when I plugged it to the player, the tracks were there on the contents folder but the playlists etc did not show, I had to go to individual folders via artist, album and then play which was very frustrating. 

I always carry a backup pen that I have just copied and pasted with and I am unsure why this keeps happening, I have used Kingston DT50s, SanDisk Cruzers and Corsair drives. Every other DJ I know does not have any issues with it. Due to these unfortunate events its very difficult for me to prepare for a gig, I keep googling the format methods, allocation sizes etc and I always eject usb properly hoping nothing would go wrong, once or twice it did work though but that's not enough for me to trust it. 

Could someone tell me what I am doing wrong? I have a gig coming up next week and I am playing on a XDJ RX, I do not have players with me to test it before I actually get there. I have my backup pen but I do not have the playlists in it and I have over 1000 tracks which makes it impossible to browse. I am currently trying the sync manager and the tracks are being exported but I might download a few more within the week. When I do so, should I reformat the pen and export again or depend on the sync manager cause exporting takes alot of time. 

I also downlaoded the app to my iPhone and I am planning to use it as a backup as well, please give me your insights on using the phone app to play, does it have a file limit etc?

Sorry for the long post, thank you for the support! :)