ok here is the background on why I’m asking this if someone else has a better solution.
Went away with my kids on vacation and I brought my roku with plex on it. The TV at the resort’s internet connection was spotty at best. We couldn’t stream anything without it cutting out.
SO I was thinking I have a 2 terabyte USB stick is there some way to install plex on it and the movies?
storing your server’s data and media on a thumb drive will give you just that… plain data/media. You’ll need some more if you want to actually run PMS (namely a machine that’ll run your server).
Have you considered watching media on a computer using Plex for Windows (or Mac / Linux)? Those support downloading media from your server to the device and play it while having no access to your server from the device.
I hear the Nvidia Shield can serve as a server. I’ve thought of looking into setting that up to run as a server using an attached external drive, then taking it on vacation. I hope I’d be able to use the same Shield and play using the client too.
Hotels are notorious for having terrible Wi-Fi. Why no option for downloads on a Roku or Fire stick?
My Firestick fits in my pocket but it’s not considered a mobile device. 
If your laptop has an HDMI port you could plug it into the tv after you download the video you want. I’m going to assume multiple people watching one laptop isn’t ideal.
You could also download it to a computer or phone and try to cast it directly to the TV or through the Roku. Depends how bad the Wi-Fi is I guess
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