Yes. It definitely is possible to do in advanced roadmaps. We're doing 5 different teams and 3 different products all at various stages of development. Roadmaps is helping us to prioritize across those projects and the capacity planning is helping us to understand when things will get accomplished (if it's not waterfall).
We are using a combination of story points for SW and straight timeline for Waterfall (but not using working hours). I'm not sure if you can do both there.
There are definitely limitations to advanced roadmaps and some concepts that are hard to get your head around without seeing them work in the SW. I highly recommend making a copy of a couple projects, sticking them into a plan that you can experiment with, and seeing how those things work. The one that gets everyone is "Resolution" -make sure it is marked as done when you close an issue or it disappears. Also, nothing gets moved automatically. If you don't finish something, Roadmaps doesn't automatically extend anything. They expect you to use automated scheduling but I got burned one time and I just need to bite the bullet and use it again.
As far as filtering, they do not filter by custom fields. You can do it by project, team, labels most importantly, and a few others. This has made it difficult. I personally hate labels for anything beyond temporary. But, I have used automation to turn my custom fields into "labels" so that I can filter on those. For example, I have milestones as a custom field so that we are standardized, but then I have automation to turn a milestone into a label. That way, I can filter by that milestone across my projects.
Good luck and ask questions.
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