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All these answers are in the documentation somewhere, but I'll answer what I can
1a. Guest access is only available on a Core License, so not all Server installations have Guest access. Online can connect to on-prem data sources using Bridge. So the differences aren't really that great. The biggest differences I see is cost and version number. Server - you have to pay for the hardware you're running Tableau on and upgrade your version when you want. Online - you don't pay for hosting, but it's upgraded by Tableau when they decide to upgrade (usually 24 BEFORE the new version is released)
1b. You can't create your own schedules on Online, so if you want to refresh something every 15 mins, you can't do that - you can on Server. There is some other minor differences as well, but nothing I can think of immediately.
2a Magically behind the scenes You can't see or control this at all
2b None of those. You can't see any hardware specs with Online, you don't actually need to. BUT in Australia we do see when refreshes take more time in the afternoon which aligns to 7am-9am EMEA time - meaning there's more refreshes using Online resources.
2c. None, but that's the beauty is that Tableau does it all for you.
3 I don't know the specifics on any of this, but I would doubt you can see anything on S3.
4a. You usually get an email a few days before to warn you of the outage. The duration of the outage and the effect of the users is clearly communicated. There is usually a small downtime window.
4b. Sure, these days the Server vs Desktop versioning is less critical, but once the server is upgraded you can only access the new features by upgrading Desktop as well
4c For Online ? NO, you have no choice. Tableau tells you when they are upgrading and that's it. If you're running Server you can upgrade when you feel it's necessary
4d Corporations handle it in different ways, it depends on your SOE strategy and how much access users have to install new software
5 Hmmm ... yes there is restrictions with Online. It's something like 10GB per user but please check that number before quoting it.
6 Unsure, I've only ever used named users when using Online.
Just wanted to say that we use Tableau Online for our enterprise, and it's fine except that the multi-tenant isn't done right. Server compute resources are not logically isolated between tenants, so we've waited over 90 minutes at times for our refreshes to run because some other tenant was running them. It's absurd.