I tried, before the crash, to take 80% equity out to buy another unit but had zero luck at securing traditional funding through a bank.

You’re entering an inflated market where experienced investors are talking constantly about the dearth of deals and you’re surprised that you couldn’t get a zero down loan from an institution.

In my case, I had a 'pre 1985' policy which falls under different funding limits, allowing more cash to be put in than current plans.

Initially buy under your own name and get sufficient insurance through an umbrella policy. 

My thought is the first step is to clearly define your objectives i.e long term vs short-term, emphasis on cash flow vs. appreciation, risk tolerance etc...Once you have all of that clearly defined, your path becomes more clear and defined.   

Not impossible though.I have private lenders who loan small amounts like this for a year at a time, but they have reasonably high risk tolerances and a whole lot of trust in me as a borrower.

Not sure if this is the right spot for this but if you've seen any of my other posts you know I'm a newbie (zero properties so far).

This deal seems to be turning into zero cash flow pretty quickly.  :-(  

That makes zero sense to me if there's not a massive value add opportunity here, which it sounds like there isn't.

This is a zero sum game.