Thanks for all the input everyone!
@Leon Y. , I've already refi-ed my SF condo, I'm on an 5/1 ARM at 2.75% that goes adjustable (LIBOR + 2.50%) in 2017. If I were to rent my condo out, it would cover my mortgage, taxes and HOA, but with only $200 or so left over. But most importantly I'm ready to move out of SF and don't have much interest in maintaining a rental property here.
@J. Martin , My place is pretty small (1 bedroom, 654 sqft) in downtown SF. So yes, the place is small and the area isn't that great, but it's increased in value almost $250K over the past four years so I'm ready to sell and walk away.
@Elizabeth Colegrove , I guess I'm "risk averse", and despite a > 800 FICA credit score, I'm not sure how easily I'd get a reasonable mortgage since I'm hoping to use the rental income to replace my W2 income within couple of years.
My basic goal is to purchase enough units (1-2) within two years to cover my day to day expenses until I start drawing from my retirement accounts and portfolio in my mid 60s (20 years from now.)