A big factor for this approach was that we were heading in the housing bubble and the numbers no longer seemed to make sense to us so we stopped buying.  

I can tell you that the office building is the most work by a factor of 10.  

Until you factor in opportunity costs as you'd have to pass on potentially great deals because you've tied up your cash in 1 deal.

I want to start investing there to increase cash reserves however I have an end goal of buying and holding multiple properties that are free and clear in order to sustain a comfortable, but not lavish, lifestyle for myself and my family. 

@Joel M.The key isn't just that its a 30k home - its what other important factors are specific to the property to make it a decent deal or not.

Just don't rationalize lifestyle inflation with the extra money.

So I imagine that factors into your calculations.

Finding investments that fit your lifestyle and marriage is key....maybe just a single family with an accessory is a baby step to see the rent checks coming in...

If you factor in closing costs it might be 3 years to start showing your benefits of a refi

Not to diminish their importance but aside from the legalities, ethics and complexities involved, if you have actually done subject to's, what are the overwhelming determining factors that would make a property a candidate for a subject to?