Here is my response. I am not a tree expert, but I have did do some research a while back to help with my own tree solutions.
A healthy pine tree will have some dead needles. These older needles are on the inside part of the branches and are shed in late summer and early fall. The tips on the branches of a healthy tree are the newest needles and are greener. If there is an excessive amount of dead needles, especially at the ends of the branches where the young new growth should be, it is a good indicator that the tree is sick and ailing. There is more than one possible cause - drought stress is one of them, but so is waterlogged soil. Other possibilities to consider are nitrogen deficiency, insects, air pollution or other types of diseases. It will take some work to pinpoint the exact problem. Something to consider is that transplanting is very stressful for a tree. It takes time for a tree to recover from transplant shock. If the tree was diseased and weak to begin with, it will need even more time to recover from transplant shock or it may not recover at all. It is important to transplant correctly and at the right time of year. It seems like you did not transplant at the right time - fall is best. Spring is not the best time to dig up and transplant a tree that is rooted in the ground. It is important to preserve as much of the root as possible when you dig it up.
It sounds as if you are needing a quick solution. I did some tree research a while ago to help with some of my problems and learned a great that way. During the research process, I learned about some preventive tree care that I hadn't even considered. For example, cleaning dead needles from the inside of the tree helps bring light to the the tree branches and is a great mulch for the base of the tree. The dead needles mulch helps the tree preserve its water during drought conditions. An isolated tree in a yard is different than a tree in a forest. A forest is a large network of trees that depend upon and take care of each other. An isolated tree does not have the benefit that the other trees normally would provide.
If you purchase a tree that is established in a pot, it can be planted successfully in the spring because the roots are minimally disturbed by the transfer from the pot to the freshly dug hole in the ground. Digging up a tree that is establish in the ground is very stressful for a tree and should be done carefully so that the roots are minimally affected and should be done in the fall for best results.
You transplanted your tree twice. You state 'before winter' for the first transplant, but you do not state precisely that it was in the fall. And then you transplanted the same tree again the following spring. Successive transplants that are close together and at the wrong time, such as your transplants appear to have been, are very stressful for your tree.
ISFP "The Artist"