Here's the question I always consider regarding reincarnation: As far as I, the entity composing this post, am concerned, what is the difference between:
(1) dying, and sometime later having my soul reincarnated as another person, with none of my present memories; and
(2) just dying, that's it, and sometime later some other different person being born?
What makes the "reincarnated me" in the first case any different from the "other random person" in the second case? Neither my present life experience nor the other person's future life experience is affected in any way, one way or the other.
The way I see it the soul does retain some memories, but they fade. Just as our human memories do. It seems reasonable that we retain a few key memories. With time we retain the lesson and not the details (such as who were once were, and where we once were, and who we associated with).
For a while the soul has an interest in those close to them, and can perhaps offer guidance in the form of "intuition" or perhaps even dreams.
A while after my late wife died, I tried internet dating. My late wife said that I did not do too well without a woman, and she would help me find someone. I went on a date with a woman that was very pushy and clinging. That night I dreamed that the woman was a giant spider in the bushes, and as I tried to get past on the path, my arm touched her web. The more I pulled away the more I got entangled. You can imagine the rest. My first and only nightmare, except I was not excessively fearful.
Perhaps that was my late wife trying to warn me. Boy, did I have trouble with that one pestering me. This is a long stretch of the imagination. But I am trying to illustrate the how such "help" could possibly manifest.
I think that I might "meet" my late wife after death, and that we could interact. That might include some other (good) people I knew.
Let me go a little further. It seems to me that souls (like God) have no gender. This means that a soul could reincarnate as a male or as a female. Perhaps one does the male thing for a while before switching to the female experience. I know that although I am an alpha male, I have a female side to me. I prefer the company of women, even if I am the only one in a rowdy bunch. They forget I am a male, and relax. When younger I was into male sports.
This could account for the all the current gender issues. Or I could just be wrong on this thinking.
(One can introduce experiential differences by embellishing the concept of reincarnation with some form or another of cosmic credit scorekeeping, e.g. karma or "soul evolution." That requires a system to turn events into records, some stable form that preserves the records, and some kind of individual identifier attached to the soul itself that associates it with an individual record, none of which is necessary for the basic concept of reincarnation itself. In that case it's the mechanisms of that record-keeping system, and the evidence for it, that should be evaluated, rather than yes or no on reincarnation per se.)
God has a big enough memory, and can multitask (being both male and female). I think he keeps score, and makes decisions as to which soul goes where, although there might be a few very advanced souls helping him.
I got the "information" about being judged when I was a teenager and twice dreamed I died. I was judged. Sent back the first time, and condemned to cease to exist the second time. One could argue it was my upbringing. But I was a firm atheist at this time. The other contrary scenario was ceasing to exist. Where did that come from?
Nothing in my dreams seemed to relate to stories and tales I had heard.
Leaving the fanciful invented celestial bureaucracy out of the picture, the experiential equivalence between reincarnation and no reincarnation works both ways. That is, to the extent that the prospect of reincarnation is comforting, the prospect of individual annihilation alongside the continuation by others of life in general should be equally comforting. And to the extent that the prospect of individual extinction is frightening, the prospect of reincarnation should be equally frightening.
Some people are frightened by change and things they do not know. I think most people are afraid of the terrible pain when one dies. If one drowns or is buried alive, it must be horrible until oblivion arrives.
Personally I accept that there is nothing I can do about it. I am rarely afraid.
This has long been something I see as wisdom. I gave it to my daughter in a time of stress in her life, and it was a big help. One does not need God to follow the advice.
https://en.wikipedia.org/wiki/Serenity_Prayer
God, give me grace to accept with serenity
the things that cannot be changed,
Courage to change the things
which should be changed,
and the Wisdom to distinguish
the one from the other.