Of course, seek legal advice as these techniques may not work in your area!

Him and his wife have been surviving off the proceeds of it, has gathered some income, but (the main challenge currently) he's a Depression era person who's seeking "secure" investment strategies.

Welcome to BP; this is an excellent arena to gain any type information you seek.

After buying our first 2 properties with our own money, we are seeking to use OPM for our 3rd house that we just "bought" - pending inspection.We have a private money loan set for our down payment + closing costs which should be roughly $25,000.

Should I seek more lenders to see if this works elswhere?

Does anyone know if there is a good way to seek out banks that have loss share agreements and try to strike deals with them that can be flipped ?

Seek legal advice from an experience Estate attorney.

As I shared this with an elder coworker today, he said everyone has to find their niche, and this young guy had his hand in many things, seeking to find that.

It is always good to check into your local jurisdictions, and if there are penalties, I would just chalk it up to the cost of doing business.

In other words, borrow 40k for 54 days and return the full 40k on day 55 with no penalty?