I don't think there is the slightest bit of inconsistency. The winch is a restricted area sure people can fly over the walls just like airplanes, does this mean there are no security checks when you land? The winch is the vital head of commerce in Yliakum's first level and it is well protected.
Brigands might not want to steal from the winch but I can assure you organized crime would (and probably does).
Megaras and pterosaurs too are a highly regulated commodity and the Octarchy keeps records on ownership and use of them.
To address the ideas about the Octachy I can tell you what I have said in the past it is a "Relaxed Totalitarian Regime" meaning over time it has gotten less draconian, but its roots would be downright distasteful to most of you all raised in the free world of modern times.
Rivalries between Octarchs and the families of the vigesimi still exist and you will get more on that later.
Poverty is not really the reason people are kept out, it is volume control. The Octarchy knows better than the average citizen what the needs of Yliakum are. You do not need to trust them as they do not need your trust.
For now let it be known the Octarchy does not care if you think the restricted access makes sense, it has its own reasons, and the power to maintain the situation as it is.
One thing most of you forget when you long for consistency is that there are "realities on the ground" to contend with. One example is "why can't I bribe my way in?" The actual reason is simple, if such a way existed, as soon as the first money bug came everyone would just buy their way in. (also the guard is upstanding)
If it hurts your feelings that you cannot get in because you will not quest, well . . . I am not sorry.
More means to get in will come in time but what can we do? You all want too much too fast.