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

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. 

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.

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

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

: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.

Whether it's Airbnb, VRBO, FF, Zillow, FB, direct booking website, insurance relocation portals, databases from MTR operators who get a lot of insurance/corporate leads, CHBO, etc.The MTR space is still quite young, unlike STR. 

@Jhamari HoganCleveland has solid deals that are cashflow positive.

Although they are not the cheapest, they have the strongest OTA connections, the most customizable direct booking website, the largest variety of integrations, top tier customer support.Hospitable is okay for when you start out, but their calendars always drops. 

Your best bet is to establish a website and do SEO for that market.