
As you will know, littermates are nightmares. I recently read a very interesting article about American guide dogs, where they did an experiment of placing two pups with each puppy walker. Even if both were just as outgoing when they got there, on ALWAYS ended up more shy and failed the training, which is why they stopped placing more than one pup.
http://paws4udogs.wordpress.com/2012/03/30/littermate-syndrome/ This is exactly what I have found myself as well, having had to keep littermates several times.
If your pup is that stressed when going out, you have to take it even slower. I have one dog like that myself, even at aged almost 5 he runs and hides at the sight of collar and lead. I don't know what you have been doing but for pups like these, just going into areas with lots of people (we live in a quiet rural area as well) can be too much. I once took this dog of mine to a car boot sale when he was about the same age as your pup. He just sat down and shook with fear, would not move one step, and I thought I'd never be able to get him back to the car (big dog). I would instead take it slower and do things like find a quiet pub or cafe where you can sit at a table outside and do nothing but watch the world go by with the pup. Or park your car near where people are and stay in the car with doors open and pup on your lap or next to you, depending on size. And Zylkene won't harm, but can help -absolutely no reason to not try it out. Calmex is good as well and is only needed an hour or so before you are going to do something.
Finally when it came to my own really bad pup, I found there was a problem with the litter in general. Of the 10 pups, four ended up with really severe problems, and none will ever be 100 % normal, we have just had to accept that. Four are extremely good and the other two just normal, so it was most odd indeed. None will be bred on from, mine are both neutered as are most of their littermates. I mated the same bitch to a different dog 2 years later and that litter ended up perfectly normal, an absolutely huge difference -yet I did nothing different in the way I treated/socialised them. The two things that were different was the stud dog and for the first litter the bitch was vaccinated at the same time as mating. Whether either, both or none made a difference I don't know. In any event it has had to be the tiniest steps possible for those dogs, still hard work 5 years later, but there are improvements all along.