What investment will you make that will at least earn you back your $165k after 1 or 2 years, AND enable you to make those payments every month?

It would show a payment history and ownership rights so should enable him to refinance it with out a downpayment providing the equity is there - correct?  

My background has enabled me to quickly spot and accurately determine the associated costs for improving or rehabbing a property as well as properly planning & executing my exit strategies.

This enabled you to convert this unit while the tenant was still in place!  

If so, this would pretty much enable me to stay local and take a shot at my first property rather than resorting to other places.

We currently use a google spreadsheet that pulls in MLS info and Zillow info automatically and it auto-populates ARV using 90% of the Zestimate (I know...yuck...but it's at least a quick and dirty number that enables us to know if we want to dig deeper).  

All on Sub2, or is your angel investor enabling you to do cash purchases?

Also regular inspections will enable you to spot any maintenance issues.  

Without giving away too much of what is an ongoing process of discovery, this gave me greater clarity  - could I keep the property filled at the right price that enabled the investment to pay for itself?

This thread was initiated not to agree on the best return metric but as an academic exercise to enable me to understand why the annualized return (IRR) goes down over time for a subject property I was analyzing. @ Stephen Greenway correctly explained that the decreasing irr comes from holding the property and averaging more modest and sustainable cash flow returns over the long haul bringing down the initial "flip" return.