Regarding moving packages annonymouslly, ii got n idea, would work at least within a city, and perhaps more:
It involves magnetic packages. It works like this, there are pedestrians and there are vehicles.
Pedestrians would each be told to be at some location, wait for a certain vehicle to park or stop at a traffic light, then the pedestrian would discreetly grab the magnetic package out of the vehicle and then place it somewhere else, either another vehicle he was told about or if necessary some fixed place, then another pedestrain would be told to pick up the package and move it to some other place, and so on.
There would be lots of pedestrians, each receiving apparently random instructions frequently, and lots of magnetic packages being moved around between spots or carried by vehicles from one place to another. The packages would have no identifying features differentiating one from another, and they would be constantly kept in flux regardless of actually having a payload meant to go somewhere.
The vehicles would be vehicles with predictable routes, city busses, cars of people that work everyday etc.
There would be a distributed censorship resistant system (perhaps running on Freenet) that would define the instructions for the pedestrians of when and where to pick a magpack and when where to place it, the system would make sure the average density of magpacks across the network remains constant and that all packages have a decent likellyhood of eventually reaching everywhere in the network. Someone wanting to send somthing, would file a request with the system, specifying the destination, the sender would be one of the pedestrians, one day that pedestrian receives an special instruction telliing about a free magpack that they can use that will be avaiable at some location within their area at some time in the near future, that pedestrian will have a window of time to intercept that magpack, load it up, and put it back on the network.
Pedestrian should report missing packages (packages they didn't intercept or lost before being able to forward into the network) and missed deliveries (not keeping a package 'cause they couldn't attach it to the intended vehicle), the system will indenpendently analyze the patterns of losses and estimate if a given pedestrian or vehicle/location has become less reliable and adjust the routing accordingly.
Routes would be submited to the system announymouslly, and once a given attachable location or vehicle has been confirmed by enough reports some of the many magpacks will be routed thru them to test (most likelly empty ones, but once in a while loaded ones as well, seemingly at random), strenghtening the reliability value of that route based on successes.
This would only work if it achieved a certain critical mass before authorities try to crack down a given section (from a single city block to a whole city) ; with enough chaotic annonymous agents and packages moving around it will be impossible to predict when and even where a given package will be, and even if the authorities intercept one package or pedestrian the odds are they will have an empty magpack or a pedestrian without a magpack.
Some routes would have multiple intercept points, with pedestrians instructed to transfer the magpack if they do find it there and if they can, one pedestrian can't the next ones in the route will, their reports of success of failure will be computed by the system adjusting the next instructions accordingly, keeping track of magpacks to decide what orders to send to which pedestrians to keep the package in flux to it's eventual destinations.
Lost and then found packages will not be trackable by the system, but if a pedestrian finds a lost package, he is to attach it to a route attempting to leave it set to open and loose it's content, informing to the system (the magpacks would have a timed opening mechanism for disposal of any potential lost content before the next pedestrian), this way reintroducing the magpack into the network empty but without the pedestrian actually seeing what, if anything, was inside.
Magpacks might be moved between cities if necessary, given that is a possible route, like attaching to an intercity bus, or by a pedestrian with additional skills and access to a piece of luggage or the landing gear of a plane etc, these tranfers and routes only used when extremelly necessary; routes with less likellyhood of getting intercepted by the authorities, with less risk for the pedestrian etc being preffered when avaiable even if the final path is much longer (some sort of risk/benefit/cost evaluation of different paths would be done by the system to decide which path to use)
To help with the critical mass issue, lots of empty magpacks would be intentionally lost, and lots of orders to pedestrians would secretly be meant to fail; keeping authorities in wild goose chases, constantly wasting time spying on people that endup not doing anything and finding packages that are empty. Obviouslly these intentional failures being considered different by the system to not disrupt real realiability calculations.
The distribute system itself would be a black box, even if somehow the authorities managed to read the whole system at any given time, it would be white noise, once activated no one would be able to actually see inside the system, the system would run itself, it's message to the pedestrians saying enough for their current step, no pedestrian would be aware of where their current magpack originated nor where it is destined to go, people sending things would communicate with the pedestrian intended to receive the package telling them where to expect their package by means outside the network, they wouldn't know when, but when receiving a package, the target pedestrian would have been given an order similar to when someone gets an empty package to send thing, with the window being for withdrawing the contents before forwarding the package back into the network instead of depositing somthing in it.
Given the scale and complexity of this system, i guess it would be hugelly difficult to implement it right now, it's probably somthing that would exist in books and movies, but not be real in the foreseable future, but at some point it might be.