Thanks for the thoughtful comment @hidave!
It's interesting how we often dream a mix of cities and places in which we have lived. I often recognize my dreamscapes, even if the places are a "scramble" of multiple locations... often I find that I can identify where I am more by feel than by the actual visuals.
I have worked through many of these places... I no longer return to some "version" of my old boarding school because I was notified that I had "forgotten" to take one class and actually didn't graduate... and then I would be back in class as a 40-something among high schoolers. That scenario was with me for many years... and ran concurrently with a business I owner that slowly failed; that I probably wasn't "qualified" to run.
My dreams have often been the most vivid (and troubling) around the times following the loss of someone important to me... even if those losses weren't necessarily a bad thing in my life. I'm not entirely sure what our minds are trying to work through. I'm sorry for your losses... it's hard enough to lose a great love; must be even worse when it involves more than one person. I'd like to think that your presence in the boy's life will imprint on him a sense of what it means to have a positive father figure.
RE: Dreaming and the Psychology of Healing, Part II