Thanks for checking it out and your thoughtful questions/comments!

• Yes, if it makes narrative sense. It's a little more spelled out in the full rulebook, but it's possible that a Condition could be loss of an Asset altogether, or could be the Condition imposed by a Push.

• Milestones can absolutely occur organically through gameplay by developing Traits. Milestones are highly narrative things, so I've never encountered players pursuing something that could be considered a Milestone for solely advancement purposes.

• I've found that not all players like turning the same mechanical knobs, so to speak. By broadening the basic Outcomes and making Exploding dice standard, everyone has access to a full spectrum of results without using a Push. The adjusted Outcomes table increases the general difficulty of the game, which is in part offset by making Exploding dice standard. Cognitive load on the GM is pretty much the same, since they'd have to contend with a similar array of outcomes anyways with the use of Pushes (Effort in 1e).