As a U.S. guy, I'm crushed we scored so low on the confrontational
and emotionally expressive scale. We look so damn boring on the cool map! Let's see if I can move the U.S. up on these scales with some of my comments. 
First, I am not trying to antagonize anyone, knock Plone or believe my views are all-knowing. I am trying to give a different perspective (site admin) from the developers on this community.plone. If by chance anything really annoys you, let me know. Also, this is a long post.
Second, I am not a programmer I am a self-described site admin and have been working in Plone off and on for 5 years or so. However, I have a very good understanding as a Site Admin. Through the years, Iāve: taken the training classes from Joel Burton, delved deeply into the Plone code, designed and had built a document management product, and even wrote some simple archetype products. So, I am not on your level of knowledge; however, I do understand many of the Plone issues.
Third, we are most concerned with what impacts our world, so I state up front I donāt have a dog in the fight you folks are discussing. So, my comments from here on acknowledge a lack of knowledge of these deep level topics, except to say: Some smart, well-intentioned people made these design decisions: It's time to move on and identify Plone issues we can improve.
The emperor fiddles while Rome burns.
Plone is losing relevance, especially in the U.S. market. I state this because:
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The number of Plone user groups has fallen off a cliff. Seattle use to have a strong group (20 plus people each month). Now Seattle has no group at all. I went to: https://plone.org/support/user-groups. The first three groups I clicked on (L.A., Atlanta and New Mexico) they were not active groups. For the first two there was no site anymore, the third the latest update was a few years ago.
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Do a search for Plone programmers (real ones, not people who claim to be Plone programmers because they know python). Aināt that many, again, especially in U.S.
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My hosting site (WebFaction) has one click installers for many products (including WordPress and Drupal). They use to have one for Plone but they deleted it. Support told me they got no demand for Plone sites.
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Do a simple Google search: Plone (3.4 million hits); Drupal (74 million
hits). Yeah, 25 times as many!
Finally, what is my issue? Simple: Functionality that will help make admins look good by giving them the tools they need to allow them to meet the needs of their users without repeated trips to a developer. Users and admins are the final customer and should be the focus of what is done with Plone. If it satisfies a need for them, it will likely help Plone and create paid work for developers.
Towards this goal I think Plone 5 brings many improvements to the user/site admin. For example, we can now easily change the account creation form (hard as hell in P4). Creating content type with dexterity is much simpler. The P5 interface is cool. However, two examples of areas open for improvement:
a) Dexterity is a big step forward from a site admin view. It allows us to create some reasonably robust products quickly. However, as an example of how the loop isnāt closed, when you create a form and add a field set, Dexterity doesnāt keep track of what widgets are added to the new tab. All widgets are added to the default tab. With the help of @cris, I learned how to edit the xml file to move the widget to the proper tab. Why? I canāt believe it is technically difficult for Dexterity to be aware of what tab the person is working on when adding content. I understand that Plone may not control this action of Dexterity.
b) Two very common requirements of a CMS, i) being able to set publish and end dates, ii) sending reminders to users of upcoming events, are either non-functional or details are hidden that I canāt find.
i. When I add content and use the āpublishā dates. I donāt see them as working. I have a site (mckennariley.webfactional.com) where, as a test, I changed the publishing date of the homepage to a future date. So why is the page still visible to users? Quite a while back @cewing explained it to me and, if memory serves, said using a cronjob to run a wget to refresh the page would do this. Donātā quote me. This feature must work. How do I do it? (I have previously posted this and Kim said it works for him. What am I missing)
ii. For the reminder to be sent, I am working with Plone product for crontab and the āupcoming content ruleā add-on. (Trouble install crontab). I can get crontab working, but still issues prevent me from getting it to work. Thanks to the people who wrote these two products; however, we need to get it the final mile to get it to work.
For each of these products, Iāve done a lot of testing and would be glad to share all my notes with anyone interested. I am not just complaining, I am digging it, finding issues, and wanting to help fix it to improve Plone for all. For example, I am paying someone to get an important content rule (emails to group) to be updated to P5. Alternatively, after looking at the code, I proposed a possible simpler solution. If youāre interested, see:
Using Plone Rules to send emails to users based on roles - #21 by rileydog
I also maintain that for Plone to separate from the pack it needs a much better use case for document management (Document Managment - #8 by zopyx) and WebDAV (Webdav file upload content type issue in Plone 5 Ā· Issue #1237 Ā· plone/Products.CMFPlone Ā· GitHub)
The people posting have in-depth knowledge, so I donāt question the details for their use case. However, I have used Zope External editor and found it to be reliable for āmoderateā use. Based on this, let me propose a use case that I think Plone could be a viable document management system for organizations less than 100 or so people. WebDAV is key to document management (e.g. Basecamp doesnāt offer it and makes document āmanagementā a total kluge.). If the windows WebDAV is a real problem why not find a good WebDAV client that can be purchased and allowed to connect to Plone?
For Plone 3, I created a product that allowed project managers to more easily manage key documents. Using Word and templates, they would create a document (e.g. project meeting minutes), when done, they pressed upload. The tool, based on content type, automatically created proper file properties (metadata), automatically named the file, posted to the proper upload folder in Plone. Then, a parsing tool took over, parsed the Word file for properties (metadata), based on these properties, created a new content type, extracted the meeting date, meeting members, etc. and created a new content type. Finally, the action items included in the document were parsed and a new instance of the action item created on the site. The user didnāt do anything except create the document with a hand Word template. Try that with Drupal!
Plone is a beast to learn. We know that. If we add another robust reason for using Plone, like document management, we make Plone dramatically more useful. I know for the large organizations, they would want to full-blown DM solution. However, the vast majority of organizations are not large. Letās help them.
I know this was long. Hope it was worth reading.
So, thoughts anyone?