Q: When people see a deceased relative in a dream, is it their own reflection or is it more objective? Is this real communication?
A: It depends. If the person is a tzaddik, it is a real communication. If it is a regular person, it can be something just within himself.
Q: Is there an ongoing subconscious dialogue with the deceased, such as family members? Is it a only in one direction or are the deceased aware, as well?
A: Certainly it is a two way street. Parents are always connected to their children whether they are alive or in the higher world. They are here, they look and take interest in everything that happens in the family. The Rebbe used to write that when the family member has a happy occasion, they know.
Q: If the soul reincarnates, it is still connected?
A: if the soul reincarnates in a different person, there is a distance, but there is still a connection. In physics, it is called entanglement. יי
Q: I was wondering if one’s family members in this life are specifically connected to one's soul and were connected in previous gilgulim (and will be in the world to come) or if it is more "incidental" so to speak and the souls of one's family change.
A: According to the Arizal, in the more recent generations, there could be less connection at the source between souls of family members. Certainly, though, there is a connection and a definite rectification in their relationship.
Q: Is there any usefulness in bringing out events in one’s previous life in order to rectify?
According to the Ba'al Shem Tov, it is not appropriate for an individual to try to discover his reincarnations. A person's service of G-d must be done with temimut, simplicity. This is one of the basic foundations of Judaism. The more that a person connects to G-d on a level of simplicity, the more simcha, joy, he experiences. Joy is the inner trait of Binah, the beginning of the left line of the sefirot. Simplicity, temimut, is the inner trait of hod, which is the bottom of the left line. The joy of Binah spreads down to the simplicity of hod. This is the source of happiness in life. It is not important for a person to know specifically what level he is on, or what reincarnation he must rectify. If his focus is on the fulfillment of Torah and mitzvot, the rectification process will take place without his specific awareness. This is a much more practical way for a person to function in his daily life, and his ultimate goals and rectifications will be accomplished with more joy.