I can negotiate either a cash rent agreement on a per seeded acres basis, or I can negotiate a crop-share joint venture if it is in an area with a farmer that I know and trust (higher risk, higher reward with crop share).2.

.- rate of return - manageability - any other risks / rewards while comparing the two options

It's risk vs reward and opportunity costThink of it this way - each principle payment you make earns (saves) you 10-17%. 

In order to remain top of mind you need to adapt and develop systems to effectively utilize these platforms, those that do will be rewarded in the next 10-15 years.

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.