Alternatively I could buy two cash flowing properties (say $50k each that cash flow $500/month) in a cheap area and use that income to supplement my rent.

For a licensed sales person with access to FMLS does alternative sources such as ListSource bring value?

Alternatively you can look for a seller financed house that will fit the bill, local investors sell on financing often here, you just need to expand your network.

The more knowledge you have about an investment alternative, the less diversity you need (and vice versa). 

We've sprawled our way to all kinds of infrastructure, environmental, and financial problems and if we don't frontier an alternative, my children and grandchildren will be left picking up the pieces.

You, in turn, have the right to seek alternate living arrangements.

Thats not going to happen: from there I started to look at alternative means of acquiring the duplex and I found contract for deed option.

Have you looked for the Craigslist Alternatives, of which there are a few? 

Hep BP peeps,  I posted a similar thread a few years ago and am back in a similar situation.  Here in Northeast Ohio (specifically the near east side of Cleveland) SFR B/B+ rentals work great with the following model:...

Do you have a superior alternative investment earmarked?