Yeah Donna, I'm in the same position as you.  The way I'm reading this new structure is that Tableau is changing direction to eventually stop core-based licensing, forcing user-based licensing to become the norm.  It makes financial sense at their end but not from our enterprise end.  We rely on Guest Access but with user-based licensing that can't happen:  That would be a major feature loss!

I stumbled across this:  How to decide on the right mix of users | Tableau Software

More of a FYI, a very high-level of the three types to kind of help decide what type of license to get users, however, it does not answer our questions.

Okay, I spoke with my sales rep and got a better understanding.  In a nutshell, I'm no longer frazzled about upgrading

First, I was correct about Tableau moving to a subscription-based paradigm and the 2018 release is the first step that we are seeing as admins towards this Tableau goal. So in other words, don't expect this to go away and do expect it to move away from the 10.x epoch.  However, core-based licensing will remain...at least for the foreseeable future.

Second, this will allow for a mixed-licensing environment for us core-based environments if we wish to do so.  I don't think this is a bad thing so far and I hope it will be helpful when transitioning to more subscription-based licensing if a company of small size decides to transition.

10.x to 2018.x upgrade

Here's a really high level view of what changes from 10.x to 2018.x

Now, since core-based environments are impacted the most by this upgrade we are the ones who have a longer and deeper mire to wade through.  Here's how the Site roles get converted:

Some notes I jotted down about the new Site roles:

Viewer -

     can interact and receive subscriptions (i.e. someone else subscribes them)

     cannot web edit

     cannot create new data alerts but can connect to existing ones

Explorer -

     like 10.x Interactor thus cannot publish

     note: Explorer (can publish) is not "normal", it's so current Publishers won't be downgraded in capability

Creator -

     Desktop author/developer

     Prep user

     create new data connections & sources in Web Edit and edit them!

     basically the Publisher role as we know it in 10.x but with additional super-powers

About these new licenses

Instead of a TD... license designation (TD = Tableau Desktop, TS = Tableau Server) it will be a TC... one (TC = Tableau Creator).  Thus the one license key can be used in Tableau Server, Tableau Desktop, and Tableau Prep.  So that's simpler (less keys to deal with) and thus completes the "package" for a power-user.

These new subscription-based licenses are transferable so if a core-based environment decides to purchase some Creator licenses and add them to the Tableau Server they can be transferred to a new owner, like how it's done with current [10.x] Desktop licenses.  This is a relief for those who have high turnover (heavy usage of contractors, interns, etc.).

Other notes

1. “When upgraded to 2018.1, Tableau Server will display the same licensing information and site roles that it did previously until a new Creator, Explorer or Viewer license is added to the server…” <link>
   1. So this only applies to user-based licensing, correct?  Well, applies to both licensings.
2. My understanding is that if nothing changes then the licensing metric (Core or User) remains unchanged. Yes
3. It appears that the licensing metric has been made to allow mixed-licensing metrics i.e. core- and user-based together.
   1. What happens to Guest Access?  It stays.
   2. There are some features only available to a user with a Creator site role - accessing those features is why you would choose to add a Creator license on top of a Core license. <link>
      1. Such as…? The Creator ability to create/swap data connections & sources via Web Edit.  My note:  Introducing additional features that drive [force?] authors to purchase subscription-based Creator license since features are not available otherwise.  This also places additional hardship on the server, requiring additional hardware...
         

And, uhm, that's all I got but it's enough to calm my nerves   Again, if you have further questions I recommend contacting your Tableau sales rep. as it provides feedback to Tableau on how their decisions affect their customers!

The following site roles for core-based licensing in 2018.1 don't change.  They look like this:

However, once a Creator key is applied to that Server the options look like this:

Screen shots and confirmation by my Tableau sales rep

Egor Larin wrote:

 

...

PS

In official Tableau Docs there is a still Tableau Perpetual licensing mode for TDl, even it is not listed in Price List

https://onlinehelp.tableau.com/current/pro/desktop/en-us/help.html#license_subscriptions_enterprise.html

 

And for TS Licensing Overview

Correct, there are "perpetual" licenses for Desktop and Server (licensing model in my first image).

Egor Larin wrote:

 

which key have you added and how? I tried with Tableau Desktop key to add and I have that error. I haven't tried the Tableau Prep key.

Am I missing documentation from Tableau is how to on-board Creator? As far as I understand, every user with Tableau Desktop Professional license can be add to TS as Creator, so actually you can increase a capacity.

I have not upgraded.  However, it is not correct that current Desktop Pro licenses can be 'upgraded' to Creator because Creator is an entirely different license.  It's my understanding that a Creator license is subscription-based only

Gerardo Varela wrote:

 

Hmz... Once you add one of the new roles you can't add the old roles? So if I add a creator, publishers are now creators, so any new publisher will fall under the subscription model? ...

Gerardo, I believe that is correct.  However, Explorer (can publish) is equivalent to the 10.x Publisher site role.

Don't worry, you can't accidentally make the change.  You would need to explicitly add one of the new licenses.

Yes, it's hard to ask questions when you don't know what you don't know...I know!    Some of my questions didn't come to me until there was the conversation of costs, license transferring, etc.  I'm sure there will be more which is why I encourage people to ask their rep. since they will know far more than little old me   When you* learn something new come here and tell us!

*The collective-you i.e. y'all, ustedes, vous tous, ihr alle, 你们, あなたのすべて, etc.