As my colleague mentioned, it takes a good accountant and/or a good financial advisor to evaluate his options and find a suitable investment while balancing risk/reward.

Our tenant has recently gone dark - I have made numerous attempts by both phone and text to reach her due to a maintenance issue she reported.   

They will pass up numerous solid deals.

Anyone who tells you that higher reward does NOT mean higher risk is wrong.  

I think you need to either pay him a set wage to perform whatever tasks you don't want to do yourself and provide bonus' for coming in under budget or ahead of schedule (his reward for physically doing work on site).

They also have a fuel rewards program on top of that. 

Risk and reward go hand in hand, don't let anyone tell you differently. 

I know it will a rewarding in the end.

If would say what you’re doing is somewhat investing, you’re taking a small risk for a small reward but there’s still an owner in place to cover the capital repairs.

Rewards come to creativity!