I’ve been feeling a Dungeon World vibe lately that has got me thinking. Playbooks are kind of cool. How well would Milestones work with a playbook?
Characters would still find random loot, but, when they get a Milestone, they check a box to the one they want. Maybe load it with several choices so they can’t choose everything. Make it a tough decision but the player builds the character by making choices.
Session zero could be the player noting which Milestones or Paths they want. If something Really Cool comes up, they can either pass or cross one of their choices off the list. Kind of like a wishlist for D&D then a Sphere of Annihilation comes up. Wanna give up one of your wishes for this Sphere?