1. Do I need to run the FSDT Installer shortcut from my Start menu?
2. Or should I run the FSDT Live Update?
There's no difference, it's the same program, the Live Update does everything automatically, the Installer let's you choose what to updated and has many other options.
4. When do I need the offline installer and why?
When your local cloudflare node is still not fully updated, which you can verify if you notice any of the updaters is seemingly downloading the same files, over and over.
5. How do I know when there is something that needs updating? "You will notice when files are not downloaded" - I have NO IDEA when anything downloads or not
Both updaters have a text area showing everything that's going on. If you don't see anything there, just a progress bar, IT'S GOOD, it means your local nodes *are* fully updated so, there's nothing to download. The problem is only if you see the same files downloading over and over, but that doesn't affect everybody, and in a few days it won't affect anybody.
I realize this is obvious to you, because you wrote this, but it really is very unintuitive and I just do not understand the update process at all.
It's extremely easy to use, assuming the servers are not acting up, then all things breaks. That's why there's an Offline installer as an alternative.
Please release some sort of tutorial or step-by-step instructions.
https://youtu.be/24QK9Xkqejg