Just a final point, and it's market based, but I would stay away from condos as an investment property unless you are going to keep it in the family for generations and don't care about an exit strategy someday. 

The way the income or loss generated from the property will be treated for income tax purposes depends on what you do for full-time work, how much money you make and other factors.

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Provided a suitable down-size from our old home, with the ability to generate cash flow after we move out in a few years.

ROBS is designed to generate tax-sheltered income that you canNOT access for personal needs. 

My main goal is to build my real estate portfolio to generate enough passive income that I can quit my 9-5 and dedicate more time to RE investing.

They will not generate respectable revenue numbers for 99% of their listings.

Advertise it online (though this generates mostly spam for me.)  

% for 20 years.My payment would be much lower, say roughly $850, which will generate more monthly cash flow, but I'm adding 12 years of payments. 

Just to realistic expectations, you can probably generate up to about 20-25% cash-on-cash returns in good rental markets these days (I'm from Baltimore, but don't know the market very well anymore), so your $160K would realistically generate about $30-40K per year in pre-tax cash-flow.To earn more than that, you'd need to take a more active role and do some more risky investments.