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. Read more...