Approaches to Milestones, Key Dates, Releases... Versions vs. Sub-Issue? (Migrated from Roadmunk)

[J P]

Howdy all... we are eyeballs deep in onboarding our product team (4 product groups of 2-5PMs each) into Jira Software + Advanced Roadmaps. Our engineering teams have been using Jira Software for a while, but our Product Team has not historically used Jira.

Previously, we used Roadmunk, which we did not like, and would not serve our needs for operational excellence, consistency, and scalability.

In Advanced Roadmaps, we are using the following hierarchy:

1. [Portfolio] Legend
2. [Product Group] Initiative
3. [Product Group] Epic
4. [Product Group] Story

However, one feature we definitely liked in Roadmunk was the ability to add milestones / key dates for any stream of work. A couple Roadmunk articles are referenced below and at the bottom of this post, I will add a couple images for visual reference.

• Roadmunk: Working with Milestones
• Roadmunk: Working with Key Dates

As I understand it, Atlassian intends "Releases" to be used for milestones. However, this does not really work for us because it seems to create visual havoc in AR when looking at group and portfolio views. Releases seems to work for larger-scale, portfolio-wide release planning, but not all the other, variable milestones. 

For us, different workstreams have different milestones depending on scope + product group + engineering team.

Has anyone figured out alternate ways of accomplishing milestones / key dates within Advanced Roadmaps?

One of our PMs had the idea to create a sub-issue type: Milestone ... that could be associated with any issue type in a more ad-hoc way depending on need. 

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Roadmunk Screenshots for visual reference

Roadmunk: Working with Key Dates

Roadmunk: Working with Milestones