Brendan,In banking terms you might be "Risked out" meaning too many mortgages which equal "Excessive Tradelines" and those two things equal high risk.

We have about $30k of net cash flow from our 2 active properties - 1 short term, 1 mid term.

@Louis AlumbaughOne thing to watch out for is that most lenders will only only at long term lease market data on the refinance. 

When she finally paid, it was $150 short.

I'm having a hard time finding a local real estate attorney to handle our closings and contracts on the asset recovery side.

Additionally, the contract requires that the deed be recorded in the borrower’s name once the contract is paid in full, but it’s silent as to whether we have to record when we purchase the seller’s interest in the contract.

Lenders will allow up to 65% CLTV on a short term loan.

I entered into a contract to buy the land, and informed the note holder (seller) of the house I recently purchased that I would be substituting the lot as collateral in place of the house.  

Over the years I became more and more involved with some of those people and as an adult started taking them to lunch to "pick their brain" (Not my favorite term but you get the point).One of these Gentlemen I have continued to meet with and give him updates on my business.

This should put you in a good position to secure favorable financing terms.