Investing in Detroit in 1950 seemed like a solid bet.  

I am sure early on in your career you`ve made mistakes and trusted the wrong people/professionals, and I bet that didn't prove you a bad real estate professional.

Who wants to bet the daughter has maxed out student loans, they both have iPhones, and make needless purchases? 

Discuss COC return, run a financial analysis for him and a performance chart showing the ROR after multiple properties have been acquired and cashed-out... good luck.

In our market, you can self manage, with all the associated work, and out perform the LTR income.  

Have you performed an amortization analysis to see when your net earnings after depreciation starts to become positive?

If there's a hole, it may be a red flag.b) sensitivity analysis: I examine all the assumptions, and make sure I can live with the worst case scenarios.c) "Stall and see": if they are getting money over multiple years, and there is no penalty for investing later, I would usually wait so I get some real performance data, versus having to look at theoretical pro forma information.d) Recession stress test: I will not invest in anything, until I subject it to recession level stress and see if I can live with the result.

I do expect an ROI but my bet is that if I lead with value by actually trying to help homeowners (and lose potential deals in the process) that I’d build goodwill in the community and more than make up for it with:1.

@Jacopo IasielloYour best bet is to go to the top of the page under AGENTS and from there you will be connected with 3-5 agents in your area

Give it a try for two consecutive projects and see how you perform by project 3..... you will be surprised how such a small tweak to your budget can impact the overall project performance.