You will quickly find out about debt to income requirements on purchases.. where you will be "Ok , I want to buy another / bigger one" and your lender will be like - "You have too much debt - we aren't going to loan you anything else right now."  

Debt service at roughly $20K.

One solution could be a Debt Service Coverage Ratio (DSCR) loan.

There was no debt on the land and she lost the house so I swapped her the land and she kept the house free and clear..

If they have paid off property (especially if the investor is much older), they probably have a healthy stock portfolio as well :) Debt has worked for me, and I'm glad it works for you too!

A private investor will want to see a few successful deals before taking out large sums as a debt loan.

Andrey this the same deal you were posting about a few months back.. if so i would contact Kathy and see whats up.. its exactly as i thought it was.. seller financing so the debt was to the seller who then probably sold the notes to other investors.. so no recourse just bad deal 

Cash out refinances are also an option it just depends what debt you have currently and if it makes sense to pull that out.

Once I work with will even go to 90CLTV, but they lend on very strict asset classes.Another family office I work with lends debt based on SBLOC. 

Everything you said is exactly why-- debt levels, market demand, associated costs(taxes & insurance).