To Dream House Raffle or Not to Dream House Raffle?

I debate whether or not to risk heartbreak again this year.

About two years ago I entered the SF real estate game with dreams of paying my dues and one day moving on up in the world, from starter condo in the TL to renovated loft in SOMA to anything with a patch of its very own grass and an address that I share with no one (so long, 3216B). Then I heard about a shortcut. When the YBCA Dream House Raffle was announced last year I felt what I’m sure those old visor-wearing ladies in Reno—with their cups full of nickels—feel each time they pull the lever on the slot machine. “This is it. My lucky day.” I’m not a gambler. And I’m not particularly lucky with games of chance. But that only strengthened my convictions that this was meant to be. This house would be mine, there was no doubt about it. The price of the ticket ($100 last year) wouldn’t matter a bit when they handed me the keys to my new property. I say property because after many nights laying in bed, figuring out how to best utilize my forthcoming windfall, I decided to take the home, which included a separate 1-bedroom, 1-bath rental unit out back, as opposed to the $1.8 million cash prize, live in the more modest quarters myself and rent out the larger house for the time being. It was all planned. Now all I had to do was wait for my name to be called.

 

And then it wasn’t. I was crushed, and baffled at how my hunch could’ve been so wrong. Suddenly, the subject of my sleepless nights reverted back to plans to squeeze a loft bed into my 500-square-foot condo so my changing table and a crib wouldn’t end up in the dining room. Ever so slowly, I got over the heartbreak and life eventually went back to normal.

Flash forward to the present day. Like a Facebook friend request from an ex popping up on the screen, the 2nd Annual YBCA Dream House Raffle shows up on my favorite real estate blog. Ugg. You again. This year it is a $3-million Arts and Crafts–style house in Noe Valley. With four bedrooms, four fireplaces, a lush, landscaped backyard (with hot tub) and, of course, a rentable one-bedroom, one-bath in-law, it is hard not to fall back into lust with the idea of my real estate empire. To complicate things even further, I realize that the house and I had a past: I had drooled over it four years ago when CH+D had covered its dramatic renovation in August 2006. The ticket price has been upped to $150, the cash prize bumped down to $1.5 million, but the dreams all look the same to me. Maybe take the cash, pay off my mortgage and invest in a rundown industrial space to renovate with my favorite architect. Or take the property, live in the in-law, rent the house and watch the money roll in. Pick up a few more places, fix ‘em up and rent them out, too. From design writer to landlord, it could work.

While I still have reservations, I’ve definitely got the Dream House fever. And the chance to get in on the Early Bird Raffle ends tomorrow. Do I live and learn, keep counting my pennies and wait for the day I can upgrade a couple hundred square feet, or do I give it another go and hope for the big win?

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