Personally, if I see a property that went back on the market after being under contract, my first assumption is, 'What did the buyer find wrong with it?'

I certainly could be wrong about that :).

Of course things can go wrong. 

Unless I’m understanding this wrong?  

Investing in the “wrong” area.  

Your savings is good, but your income won't support that many properties if you do them wrong and need to carry 15k min reserves for each one.Focus on what the next property should be, maybe upgrade to a two-family and see how that goes.

There's  nothing wrong with investing in syndications if you are writing smaller checks but perhaps invest with the syndicator who is chasing your checks because you are the only option, not the preferred option.

But here are some really interesting numbers...Ok so this one doesn't look too bad but notice how much more the townhouses and condos dropped in prices over the last downturn.2007 peak to now isn't so good...Before the 2007 run up to now is better, but even then, apartment condos performed the worse (so best case scenario, you have the worse performing asset type, worse case scenario you had a terrible return), and that's assuming you had nothing go wrong with the condo (special assessment etc)But benchmarks don't even tell the whole story, because if you had a specific condo investment, and you tracked it's value overtime, benchmark prices isn't the right approach as it evolves overtime (benchmark price is the price of a typical property generated at each point in time).

An Appraisal is just an opinion, it can be very wrong either up or down. 

Unless I was reading it wrong, you don't have liquidity to do the repairs to your current house which would increase the value and the rent and you also don't have capital set aside to buy a new home without a sale contingency.