First off, thanks all for your advice. Please see my responses below. Appreciate the dialog!! Apologies for the long-ish response - hope you guys don't get bored reading it :-).
Bob - I want to believe (I certainly hope) that bay-area prices keep appreciating over my life-time (and I'm in my 40s). My concerns arise out of sustainability - how long will this growth sustain? I feel like new folks are practically priced out of the market - and this will eventually affect the job-market. - BUT this is anyone's prediction, really. I'm fairly certain - long-term it would all be fine!
Brandon - Yep! you are correct...I'm not in trouble or desperate for money at the moment. But after buying house #2, our cash-reserves have reduced quite a bit... I'd have to peruse the biggerpockets forums a bit more, to venture out of state...but the prices sure sound tempting compared to the Bay Area. Wow!
Wes - The math started to become a bit complicated for someone new to the game, like me. IF I sell house #1, I'd have to plow the proceeds into reducing the mortgage on house#2 - since $1M+ interest carries no tax benefits :-(. Then after getting to steady-state (~2 months after close), I'd look for cheaper properties either here or further away like Brandon suggested. Also, I'm getting an accounting crash-course from reading online. Depreciation while renting, depreciation re-capture at sale, LOSS of the 500k cap-gains-free provision if renting beyond a certain period of time...Oh man, the list goes on...
Greg - As I described with a few $-figures in my original post, if I rent the property#1 out right now, I'd have a positive cash-flow of approx. $1500-$1700 / month. So I will make money, just if I look at this property alone. Of course - this assumes I'll have a renter each month - but right now, the demand for good-schools is solid. and yes, house value at purchase was just under $800k. BUT - you are correct. With 2 mega-investments (by my standards) in two different houses - I worry a LOT about a 2008-repeat, OR a BIG earthquake in SF... :-(.
Thanks again, all!
-R