these are great questions! it shows you are getting to the understanding of Teleport. At first sounds simple, then becomes confusing, then almost simple, but always some extra twists to prevent the feeling of full understanding. I think this is due to knowing that you cant know and this is not normal in crypto or computers or finance.
The privacy level has quite good properties, especially since it increases with overall activity (unique among all anon solutions), but each tx is still done the same. Add in M of N and it eliminates packet sniffers, especially due to the probabilistic routing and random onion layers. I was thinking of randomizing M of N for each telepod, but too messy and so each teleport will use the same M of N for all the telepods of the total transaction. Just when you think it cant get any better, you add in the trusted teleport path, which is basically a wild card. Anything can happen via even the smallest trusted teleport paths. There is really no way (short of actual physical surveillance and taking videos of you on your computer!) to know where the telepods are going via trusted teleport as M of N sends them in a random patter across the network, it bounces around and ends up at the destination (all protected by layers of encryption) and then there is NO cloning event, so the statistical analysis has no data to correlate. Like there not being a permanent blockchain that is vulnerable to future computers, in this case there is no blockchain event. Of course the possibility of double spending is there, and this actually brings to doubt if you really sent a payment or not, even if it was found out!
Does receiving a telepod and not cloning it mean you got payment? Plausible deniability kicks in. where is the money? it is technically in both sender and receiver's, so it is split. Now it can spread from the receiver to others, but maybe it is split into smaller pieces, so the whole things gets very fuzzy very quickly.
I would hate to be the guy tasked with trying to crack Teleport, I bet he will end up hating me
James