Milestone levelling causes me more problems than it solves.

There. I’ve said it. I’ve chosen to swim against the tide.

I love the concept of milestone levelling but the reality is somewhat different. Currently I’m running two D&D 5th Edition campaigns. One is Curse of Strahd (milestone levelling) and the other is Tomb of Annihilation (XP levelling). My previous campaign was XP levelling as well and it worked fine.

Now, I should mention that I play pretty much entirely via Fantasy Grounds, so a lot of the book-keeping of traditional XP levelling is automated for me. This is a very good thing. I’m also not entirely at peace with XP levelling either. I regularly struggle to figure out how much XP to award for incidentals, good role-playing or inventive solutions. I also have players who miss sessions so they often level more slowly than other party members which can create some disparity, especially at lower levels.

So, XP levelling isn’t perfect. But it’s more perfect than milestone levelling in my eyes.

The main problems I have with milestone levelling are as follows:

  • When to level? Adventure modules such as Curse of Strahd make suggestions about story events which cause a level up but they suggest more story events than there are recommended levels in the adventure. The party run the risk of outgrowing their environment if you follow the suggestions to the letter. As a result, as a DM you end up picking and choosing major story arc completion points which result in a level up. Which leads to the next problem.
  • Player expectation v DM expectation. It’s difficult to balance when the players expect a level up as a reward with the DMs reality. The DM obviously knows what’s coming, while the players don’t. It could be that you plan to award them a level up in the next session but they feel hugely aggrieved because they feel they deserve it this session. The bigger picture isn’t available to them.
  • Multiple levelling triggers can be reached at the same time. My party in Curse of Strahd has (within one session) finished clearing Argynvostholt (they were at it for weeks) AND found the second missing gem for the Wizard of Wines Winery. Both of these are identified in the book as levelling points and deservedly so. However, I’m not going to give them 2 levels at once. Which feels fair and unfair at the same time.
  • Pacing. With a sandbox module like Strahd, it’s hard to know exactly how many sessions it’s going to last. They may complete everything or miss entire sections of the adventure. It’s tempting to spread the levelling across the whole campaign time span, but without knowing how long this is going to last, it’s difficult. Level them too slowly and they are going to be easy prey for the denizens of Barovia. Level them too quickly and they stroll through the adventure. Neither of those things are fun.

I’m too far through Strahd now to revert to XP levelling without it jarring but I’m very glad ToA is XP levelling. I’m on largely familiar ground with that.

I’d be keen to know your experiences with either XP or milestone levelling. Feel free to comment below.