Although my parents did well, it was very much a roller coaster, and I've got a few scars.  

It took the guess work, will power, and emotional roller coaster out of the equation.

LOL hopefully he comes through with the money to pay you back and this will just be on roller coaster of a learning for you.

Just search the forums for "Morris Invest Case Study 2.0" and you'll find my year and a half detailed account and 700+ comments of the roller coaster journey I was on.I've since sold that house, but changed my investing strategy and bought another single family a few months ago.

I'm currently working a project similar in scope - I can relate to what you were saying about the mental and emotional roller coaster when you are in the middle of it.

I'll always buy used, maybe creep a few years newer as things progress but for now I like them 10+ years old after the value has taken most of its ride down the depreciation coaster. 

Likewise most on BP would say don’t buy mutual funds because you have no control over your money , the returns are poor , and it’s just another part of the market roller coaster we avoid .

Yet) Rich Dad Poor Dad, Millionaire Real Estate Investor, Multi- Family Millions (Dave Lindahl), ABC’s of Real Estate Investing, The Book on Rental Property Investing, Hold, The Advanced Guide to Real Estate Investing, The Due Diligence Handbook for Commercial Real Estate, Millionaire Real Estate Agent, The Book on Managing Rental Properties (Brandon Turner), The Emyth Revistited Crushing It in Apartments and Commercial Real Estate, Emerging Real Estate Markets ,The ABC’s of Property Management, Wheelbarrow Profits, The One Thing, Outliers, Start with Why, David and Goliath, Chasing Excellence, Extreme Ownership, The Compound Effect, The Entrepreneur Roller Coaster, Be Obsessed or Be Average, The 10x Rule, The Obstacle is the Way, Ego is the Enemy, Am I Being Too Subtle, 48 Laws of Power, Atlas Shrugged, Man’s Search For Meaning, Sapiens, Tools of Titans, Four Hour Work Week, Who Not How, Shoe Dog, Ride of a Lifetime, The Honey Bee, Living with a Seal, 10% Happier, Relentless, Zero to One, Can’t Hurt Me.

This is why the Fed is stepping on US neck more and more trying to choke things out, because they would rather get a roller-coaster effect from recession, boom cycle vs stagflation. 

I have put days of work into helping her understand the process, answering question, going through her emotional roller coaster ride, etc.