Am I thinking clearly about Cloud?

So I have PMS currently getting my OTA via Tablo, and TabloRipper and all is going nicely. Now I find I need to go to an alternate location for a couple months, and I know I won’t have any joy watching my PMS remote (double-NAT is first problem, but even if I overcome that I only have 1 Meg upload speed!)

So wondering if it would work to put my “My TV Shows” PMS library in a Dropbox or Google Drive “drive” on my PMS, then be able to watch while remote using the Plex Cloud app while still being able to watch from the local copy on the PMS while at home?

The DropBox drive on the PMS server (Windows 10) should operate like any other drive / folder on the local machine, with the exception that it is synced with the Cloud DropBox space. When watching the local Win10 PMS, it would still be on a local drive.

But when watching during my remote time, I could get it from DropBox and not be limited by my 1 meg upload… other than it is likely to take a while for a new program to get to DropBox, but I’m usually a few days later watching anyway…

Am I missing anything glaring?

TLDR - Summarized
What Cloud sync is and isn’t - https://support.plex.tv/hc/en-us/articles/201889756-Cloud-Sync-Overview
Covered in link above;
You’ll need Plex Pass to use it. Some clients don’t allow for it
You don’t drop files on your cloud shares, you place files locally then set Plex to optimize/sync them to the cloud shares.
https://support.plex.tv/hc/en-us/articles/202045106-Settings-for-Sync-Jobs
To watch the content, you don’t need access to your remote server.

Your server uploading new content may not work because your client device can’t talk to your server remotely to tell it ‘yeah, i watched that, make sure to sync the next’
Bottom of this page https://support.plex.tv/hc/en-us/articles/201059637-Sync-Multiple-Items-Dynamically


Long read -
You wouldn’t place files anywhere but on your local drives, then you let Plex sync them for you to the cloud provider you choose.
Additionally, Cloud does require a Plexpass.
Read, and maybe re-read, the bold sections of the Plex Cloud overview at the Wiki.
https://support.plex.tv/hc/en-us/articles/201889756-Cloud-Sync-Overview

As for accessing the cloud library later, I’d recommend testing while away from your home LAN before going away on your extended trip. It’s possible Plex.tv has to be able to access your server remotely to know what’s been synced for your mobile.
And unless a more experienced cloud user comes here and confirms ‘yes or no’, I’m not aware if a synced library gets synced again when new content is added.

EDIT - Ok, I just re-read it myself. As long as you let Plex sync your content, you don’t need to be able to access your server.
Plex.tv will know and tell your device ‘use the cloud’.
As for if sync’ing will update/send new stuff added later, I still can’t find any indication in the Wiki.
From all the language, it seems to be a one time thing.
https://support.plex.tv/hc/en-us/articles/202045106-Settings-for-Sync-Jobs

@ilhoelx
EDIT2 - Ok. Found it! Finally. Wow it’s buried.
Bottom of this page https://support.plex.tv/hc/en-us/articles/201059637-Sync-Multiple-Items-Dynamically
So, according to that last step statement, any new content will be uploaded if using the On Deck.
However, that’s still a challenge for you. You have to ‘sync’ with your local server so it knows what you watched.
If you can’t access it remotely, it may never know to put new stuff.

Thanks @JamminR