Selling real estate is always a personal business, considering that you work with people.

But when you work with family, it’s even more so…

A few weeks back, I told the story of my dear “Auntie Faye,” (now let’s call her “Ellie”) and how she was unfairly targeted by a local agent who pulled the old “I have a cash buyer waiting to purchase your home,” when in fact that agent was just setting up my Aunt for disappointment.

You know the drill – you promise to bring a buyer, and when that buyer never materializes, you say, “Well that didn’t work out, but we have such great rapport , so why don’t we list your house on the open market?”

The agent, who I can’t name, works in The Beaches, and has a reputation for being shady.  She’s an awful woman with no moral compass and I have no clue how she gets clients.  But I digress…

After that experience, I sat down with my Auntie Ellie and her husband Larry, and we talked about their real estate goals, both short and long term.  Talking about real estate goals at this phase of one’s life cycle was tantamount to talking about life goals, but it needed to be done.

Here I was – at 32 years old, sitting down with my Auntie Ellie who helped raise me, and it was now incumbent on ME to take her from a large, half-empty house and downsize her into a condo.

And this is where the “personal” element of real estate takes on a whole new meaning.

My Auntie Ellie is my mother’s younger sister by about three years, and growing up, our families were inseparable.  So much so, in fact, that my cousin Amber actually attended Bessborough Public School in Junior Kindergarten with my sister, Julie, even though Amber lived in the Beaches.

My Dad and my uncle David were very close as well, as they felt like “outsiders” amongst my Mom & Ellie’s family, and they grew close as both couples had children and built families.

We grew accustomed to going to movies together, having dinners together, and often vacationing together.  My brother Neil and my cousin Katelyn were two years apart, but they were both the “babies” of the families, and they were joined at the hip.  My sister Julie and my cousin Amber were born only two months apart, and were also a dynamic duo.  I was right in the middle, but I felt like I had two older siblings, and two younger ones.

Many of my earliest memories took place in Auntie Ellie’s Beaches house, as well as down on the boardwalk and at Kew Beach.  Ellie was like my second mother, and was tasked with babysitting the five of us kids many nights when my parents were out, although my Mom was often given the same unfortunate chore to make amends!

Our lives changed significantly in 1987 when my uncle David passed away very abruptly.  It’s been a quarter-century since that fateful event, but in my mind, it still feels like yesterday.

I remember sitting upstairs in the den – surrounded by Beta-max cassettes (my Dad and uncle David thought Beta would beat-out VHS in the cassette wars), when Auntie Ellie took me aside and said, “Your uncle David passed away.”  I didn’t know what this meant, and she further explained, “He died.”

I remember seeing Neil & Katelyn playing with dolls (sorry Neil…) on the floor nearby, and I asked Ellie, “Why don’t they care?”  She told me, “They’re too young.  They don’t understand.  But you’re a man, David, and you understand.”

Yes, I was a man, at age seven, but I still couldn’t grasp the fact that my uncle David was gone.

My Dad was impacted especially hard by uncle David’s death, as my Dad’s own brother, Rick, had unexpectedly passed away one year earlier.  First Rick, now David – two of his family members and closest friends.  At 39-years-old, my Dad’s world made absolutely no sense.

In my mind, uncle David was 7-foot-4, and 300-pounds of muscle with hands the size of baseball gloves and a bald head like a bullet.  Last week, Ellie laughed and said, “I think your memory is playing tricks on you.  He was about six-foot, ish.”  But I remember uncle David picking up Amber & Katelyn and placing them on both shoulders!  Only a giant could do that!  I was also pretty sure he carried a sword and a shield at all times, but maybe Ellie was right and none of that ever happened…

Amber was nine years old when her father passed, and Katie was two, and their lives changed dramatically after this.  Whose wouldn’t?

I remember my Dad trying to involve them in our lives a lot more.  Amber came on ski trips with us, and she became a part of our family.  We went out for Sunday dinners to “Spadina Garden” on Dundas Street in Chinatown, and our families rented a cottage every summer for the next decade.  My Dad treated Amber like a daughter, and if he bought Julie shoes, he bought Amber shoes.  Amber and Katie were like sisters to us.

My Dad, brother and myself were really into collecting sports cards in the late 80’s, and we were always on the lookout for any Aurel Joliat hockey cards from the 30’s.  Aurel Joliat, a former Montreal Canadien and member of the Hockey Hall of Fame, was uncle David’s grandfather, and my cousins’ great-grandfather.   Somewhere, Amber & Katie have about a dozen of those hockey cards…

Once we all became teenagers, we grew apart, as most cousins eventually do.  We went off to school in various small cities across Ontario, and reconnected maybe once per year as we moved into adulthood.  But at 32-years-old, I remember vividly how close our families once were, and those are the most cherished childhood memories I own today.

And now in March of 2012, Auntie Ellie called me and asked for my help downsizing.

Here I was, a child in her eyes – the same child that once painted the coffee table with White-Out, and I was responsible for finding her a suitable home for the next decade, maximizing the return from her largest asset, and setting her up financially for the future.

Auntie Ellie had been in this house since 1977, and it’s all she’d ever known.

How do you let go of that? I sat at the dining room table with Ellie and Larry and didn’t even know where to begin.  My mind was racing!  We had about a dozen Christmas Eve dinners here!  We used to open presents RIGHT THERE on the floor next to where I was sitting!

I glanced over to the door that led to the basement – I was always afraid of that basement as a child, I’m not sure why, but the dark stairwell and the green door somehow reminded me of my uncle David.  I never went down there as a child.  Not once.

We toured the house, and upon visiting the third floor loft, I distinctly recalled watching Grease and Grease 2, back-to-back, one night while babysitting Neil & Katie while my Mom & Ellie went out for dinner.

The rooms all felt smaller than they did in my mind.  Didn’t we used to have FIVE of us in the den, watching Michael Jackson’s “Thriller” video?  Well, I guess there were only three of us, since Neil & Katie ran out of the room once the video turned to the graveyard scene.

We sat back down at the dining room table, with me in a full suit – a very different version of the newborn baby that Ellie once held in the hospital, and I led them through the process of downsizing into a condo and selling their home.

I’m 32-years-old with almost a decade in the business, and I’m one of the highest-producing agents in the city, and not for a moment did Ellie treat me like anything but.  She respected my opinion, my plan, and took every single word to heart.  For some reason, perhaps, I figured she would still look at me like the child she once knew, but she didn’t, and that meant the world to me.

I put Ellie & Larry into a beautiful condo with a million-dollar-view for only $400K.  I introduced them to condo living (Larry thought he wanted a house until he saw a fat, shirtless neighbour eating pastrami and leaning on the mutual fence!), and I set them up in a low-maintenance home that they can live in comfortably for the rest of their lives.

And when it came to selling the house, they took every single last suggestion of mine.  It took two months to move out three-decades worth of possessions, and then we painted, updated, and listed the house vacant.

The process couldn’t have been easy on Ellie.  She told me that she found a diary from the 80’s and it fell open to an entry right after my uncle David died.  She said that she had written about ME and my reaction!  Apparently, when she told me my uncle had passed away, I said, “That’s really sad because he was a nice man and he never yelled at us!”

I cried endlessly in 1992 when my dad moved us from Parkhurst to Bessborough, and watching our family home get demolished by a developer tugged on my heart-strings more than I’d like to admit.  But imagine leaving your home of 35 years?  Where you raised two children, where you married your second soul-mate, and where you had lived for more than HALF your life?

Ellie & Larry handled it like pros, and they let me do my job.

Auntie Ellie once told me, “Many people are re-born in their 40’s and 50’s and they embark upon their second lives.”  That’s what Ellie found with Larry, and now they’re close to a much-deserved retirement, and they should travel the world ten times over.

The sale of their Beaches home represents the end of an era in their lives, but I feel infinitely connected to it, as it signifies the end of an era in my own life as well.  I’m closing the book on those childhood memories, which at 20 years old, weren’t that far off, but at 32 years old, are a beginning to fade.

As I said at the onset: every purchase or sale of real estate, and every buyer or seller represents a very different and unique personal experience.

But even after selling my own family home five years ago, I can say that this experience, by far, dug the deepest into my memory and my soul…

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P.S. I actually wrote this blog while doing the agent’s open house, and I started to cry while proof-reading it!  Some Re/Max agent came in and asked me if I was alright!  I said I had something in my eye…