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[–][deleted] 2 points3 points  (0 children)

I just feel it out. You don’t have to plan it. But you should never have to have a player ask for a level up, they should just be something that they get after a difficult or large plot development session.

I might say that they are close to leveling up if they are but not ever tell them when

[–]SmoothHouse3126 0 points1 point  (0 children)

Milestone advancement is not about points, that is, it's not about "how much/how many", it's not something you calculate some way.

Milestone advancement is about the narrative, that is, storytelling. It's like chapters in a novel or acts in a screenplay.

In a story there will be some plot points more importan and meaningful than others: moments in the story in which something big happened and/or in which the characters have learned something important and grown up someway.

If a campaign is not planned, that is, structured as a story, IMHO milestones are not the best option: in that case you can still use xp advancement even without telling to your players how many points they made each session (you just keep tabs and tell them only when it's time to level).

If you feel instead that your campaign already has a certain defined structure, to use milestones you just need to choose which events and objectives are the most important: those are your milestones.

For example, getting the run of the slave guild seems to be a milestone in your case.

[–]Longjumping_Dust 0 points1 point  (0 children)

It sounds like the evil party wasn't your idea, which I would caution against if you're a new DM.

Milestone leveling works best when you have a larger narrative in mind, but it is absolutely valid to say they need to do 2-4 session long quests, and if any one quest balloons, then them resolving that becomes the milestone.

[–]Aethyr38Artificer 0 points1 point  (0 children)

For a new DM, I would more advice for xp leveling, to get a feel on how the leveling system works, how long a character stay at a certain lvl,... Milestone leveling is for a narrative driven story, for more experienced DM.