We have a quite naïve installation of Jira and also a inexperienced user base. We are trying to impress upon the team the importance of planning upfront so we have a good view of the scope of a project.
We structure things as Epics, Task and subtasks with the Epic having no estimate. Tasks, if they have no subtasks, should have an original estimate. Tasks with subtasks should be estimated at the subtask level. Unfortunately, this isn't always the case. We often have scenarios where there is a task and no subtasks. The estimates are added to the task. If subtasks are then added, sometimes they will get estimates. To overcome this, I've created an automation that deletes the estimate from the task, meaning, in theory, the estimate for the task should be the sum of the estimates from the subtasks. Equally, if my users have added an original estimate against the Epic and then subsequently added original estimates against the tasks within the Epic, my automation removes the Epic estimate so that it becomes a sum of the original estimates of the tasks and subtasks beneath.
I am able to see this below the Epic, and this tells me that I have 6 tasks with 3 in progress, but what I want to see is something that provides an accurate reflection of the size of the Epic and the remaining time. 
I had thought that the roadmap would give me this, but even though I have automation that sets the startdate to the date of the first worklog, and I have another automation (through the API) that defines the the due date based on the remaining estimate and the allocation of the tasks (so if the Epic has two tasks, one for Jim and one for John and these are 2d and 3d respectively, if the work hasn't started it will complete in 3d) this gives me a size bar for the Epic in the roadmap, and beneath each Epic I can see how many tasks are in progress/done, I cannot see any breakdown of this.

For some Epics, usually older ones, I am able to see the tasks beneath them

but even in these cases, I can only see the task and not subtasks, and these do not include size bars along to indicate the start & end/due date.
For my newer Epics I do not have the expansion arrow for the Epic and so can't see the tasks beneath it anyway.
The key thing I'm looking to address is:
- How to ensure that expansion arrow appears for all Epics
- A view of all Epics (as per the existing roadmap) with;
- A timeline for the Epic as a whole from Start to DueDate (as per existing roadmap)
- The Done/In Progress/To Do metric (as per existing roadmap)
- An expandable arrow that drops the tasks into the roadmap and shows the same metrics (timeline and done/In Prog/To do) for each task.
- An expandable arrow that drop the subtasks for the selected task into the roadmap and shows the same as for tasks and Epics
- On the timeline for each of my Epics I want to show a marker for milestones that are defined. In my case, these are Creative Review and QA Date. Something like:

If I need to buy an Addin to do this, I can. I'd prefer to find a solution that achieves this natively, but if there isn't one, I can live with that.
Really, what I'd like to do is spend a day working through this with a Jira expert/advocate so that I can come out of it with a set up that I can enforce and manage going forward. Again, if this is a paid consultancy, that's fine.
Does anyone have any thoughts or suggestions that will get me to the point of making this give me what I need?