The main issue you haven't mentioned is that you have too many layers of roofing up there and weight is a real concern.

I bought a home with another person we each own 50% but she took off 5 years ago and hasn't contributed any money towards taxes of up keep and maintenance in 5 years.

This is not something that requires congressional approval, so the announcement today carries significant weight.

Regardless, I was able to rent it out in about 45 days and we’ve had the same tenants in there this entire time – cash flowing nicely with little maintenance and upkeep.

Do lenders actually lend on the income of the asset or it is weighted on the net worth of the borrower, or both? 

Hard money lenders will lend sometimes without doing a credit check or don't put much weight on it.  

It obviously wouldn't be ideal, but knowing I probably won't lose my hat takes a huge weight off of my shoulders. 

Meaning if yours is a flip, find renovated homes or homes with high upkeep.

We always take into account that beachfront will need more upkeep than an inland home and also insurance/price will be higher to budget for (you probably already know about the insurance part). 

The only sector I would touch right now as investment would be dollar cost averaging an equally weighted S&P etf and that would be months from today.