Lastly, do not send any funds directly to the borrower.

@Jeff Rabinowitz Just FYI, in Ohio with a land contract if the borrower has more that 20% equity or has lived in the house 5 years or more then you have to foreclose.

Here's where I'm trying to get creative:I have around $190K cash-on-hand, and I'm thinking about borrowing another $100K+ from a willing parent to possibly fund buying this property with cash. 

I would imagine selling a couple houses a year (there's a great opportunity I can discuss later with guaranteed listings), and having the borrower get financing through another bank in town, while still maintaining my normal day job.  

Depending on the strength and experience of that borrowing entity you could also seek additional collateral and security through crossing other property owned or filing a UCC over the company.

If you are going to borrow just to pay for the course, it is probably a bad idea.

Some allow lend to borrowers 2 years after the bankruptcy while others require 4 years to pass. 

My answer would depend on how much the closing costs are....if you are talking about paying $3K in closing costs to get that $30K in equity out, I would say dont do it....doesnt make sense to pay 10% for the privilege of borrowing 30K that you will then be paying 4-5% on as well.  

Keep in mind you will be borrowing tens of tens of tens (and sometimes hundreds) of thousands of dollars over a 30 year period.  

I can’t borrow the traditional way FHA, banks or any other way due to having a bankruptcy 2 years ago.