However, it does demand solid digital marketing expertise to see positive results.

For me the best-case scenario would be to pay him some cash to assign the deal, and then you take it over 100%.If you have no cash, then it becomes a question of who has the greatest position of strength. 

If you have one abuser, it won't affect everyone else systems.One thing not mentioned that could possible be a concern is were they are placed. ie. are they all positioned well for inspection and/or replacement if need be?

I've already got a salaried position which demands more hours than it pays (like they all do), so something with minimal hands on requirement in my spare time would be ideal.

I am in a position I am not exactly sure of the best strategy to take.

This implies likely over 8 years to have positive cash flow. 

Like you said, put the proper protections in place but know that you can still lose your money - unless you are in first position.

:Class A Properties:Cashflow vs Appreciation: Typically, 3-5 years for positive cashflow, but you get highest relative rent & value appreciation.Vacancy Est: Historically 10%, 5% the more recent norm.Tenant Pool: Majority will have FICO scores of 680+ (roughly 5% probability of default), zero evictions in last 7 years.Class B Properties:Cashflow vs Appreciation: Typically, decent amount of relative rent & value appreciation.Vacancy Est: Historically 10%, 5% should be applied only if proper research done to support.Tenant Pool: Majority will have FICO scores of 620-680 (around 10% probability of default), some blemishes, but should have no evictions in last 5 yearsClass C Properties:Cashflow vs Appreciation: Typically, high cashflow and at the lower end of relative rent & value appreciation.

@Jhamari HoganCleveland has solid deals that are cashflow positive.

Cash position needs to be around low $100k and I can get you a turnkey property that cash flows with property management in place as well.