Spend the time, make the effort, and (hopefully) reap the rewards.

Consider the risks vs the small reward...

Going into an area with little data is high risk but could be high reward. 

Stay consistent, set clear goals, and remember real estate is a long-term game that rewards patience and persistence!

And yes the higher the barrier to entry, the better the return (reward). 

How do you balance the risks of holding during a market dip versus the rewards of appreciation?

I presently have a negative cash flow  in all 3 properties but am more interested in paying off the mortgages early to reap rewards later.Any thoughts? 

Your risk vs. reward is way off balance there. 

If he didn't want it or can't afford it, I would have reward him with 60 days time to find another place, then find a new tenant that can pay what it is worth….  

I want to make sure that both of us feel like the deal is fair and equitable for the risks and rewards involved.Any guidance on how to approach these key questions would be greatly appreciated!