Given the quick assessment of $0 equity, maybe rehabs, deppreciating market over a few years now, is offering the Subject-To offer even viable here or should I just offer the short sale which is probably coming?

Start building a buyers list so you have people to offer deals when they come along.

Zillow used to offer Smartmove earlier.

Too small to offer good terms.

I would like to see what you have to offer and show you what I can offer....

This would become my primary residence, where I'd also be undergoing renovations as this home was built in 1950 and is currently in need of repair.My question for everyone kind enough to offer advice is two-fold:Does anyone have any recommendations on how I should perform an engineering inspection (pre-purchase)?

That way, when I pull the cash out of my house, I will have enough to offer cash on another property with the combined total of equity from my house and equity from an investment property.  

How long do you wait to offer them the cash?

If the second floor is also a two bedroom, you may not be able to offer that to them in exchange for the first floor as it sounds like it may be an issue of overcrowding.You did not mention the third floor.

@Joe Mclain yes I am willing to offer cash for keys.