You might also want to talk to an attorney about setting up a living trust for your estate versus letting things go through the court.Good Luck!

And the people who were able to get loans in the last several years had to go through a difficult process of proving to the bank that they could repay the loans so the borrowers were more financially stable then the average borrower of 2006 to 2010.  

I predominately work with out of state investors looking for cash flowing rental property in our market. 

The initial $100k negative would consume many months/years of cash flow.  

If your cash flow can't cover property expenses and/or you have difficulty keeping a tenant there for long, are you comfortable taking on the monthly payments with the car loan?

Your cost of living sucks in NYC so that hurts as well.You say you want financial freedom, but what you really want is time freedom and the only way to get time freedom is through earning money to give you that.

I like Columbus for moderate cash flow and high appreciation and Cleveland for high cash flow

We both attended University of Central Florida and lived in a house that my parents bought for my sister and I while we got through college, and the idea of student rentals intrigued us.

I won't go through with the deal if I cannot add at least 1000 sqft through the ADU construction. 

There are a lot of blog posts there to read through.