With several hiking trails/boats/kayaks/bicycles/etc, and just nature in general, what do most people do protect themselves from potential issues?

It's random, and those were just the people that I happened to meet over a couple of hours (and I'm not naturally extroverted).

Then there's other factors to success especially in a heavy lift like this, some of the most important in my opinion are Being on site regularly to manage the contracting processHaving a lot of cash reserves - 'a lot' imo would depend on how thorough your current bids are and how old the property isYou mentioned it's bleeding cash now, whatever your timeline is for the property bleeding I'd double it and see if it still makes sense. 

It seems like it's something people do on the regular, and the lender doesn't usually trigger the due on sale clause. 

What you've shown here is not really a cause for concern in my eyes, however I see much worst conditions regularly.

Property Management Company we work with right now to manage is fine with regular rental but I am having hard time working with them on student rental where some of the regular renting rules don't generally apply. 

I'd focus on getting a better property manager, their job is to shield you from most of these headaches and to prevent them in the first place through tenant selection and doing regular property inspections.

Oh and the original Incumbent tenant dies of natural causes in the unit one month prior to closing in June which delayed it again.Needless to say...

Depending on the nature of the relationship he had with the deceased, he may actually find it offensive that all you care at this point is your rental. 

Begin small by making regular contributions to build your portfolio over time.