Leave the land as it is, with tall brush, and sheds (in relatively average condition).

If the guy said I don't want to list till I find a place or similar I would brush it off and maybe trust him that he wants to move in, clean his old house up, then sell. 

Need to clear brush and plant about 10,000 trees. 

and that happens with supply demand or value add or rental rates rise significantly.these lower value areas rental rates are quite static and have been for the almost 20 years I have been playing in that sand box.. so the only value increase is if an investor will settle for smaller return the one before them. 

Why don't you just leave the rate static and use excel to run a normal amortization schedule? 

Concrete, Wire brush, not a terribly difficult job.

Yes, you could consider whether the property values in that area have historically risen or if they've remained static.

Your high cash flow areas just mean more risk, when talking broad brush commentary.  

I think I spent around $3k in 1999 clearing and rough grading (but not excavating) when I built my house and there wasn't any real timber to cut down, just a decent amount of brush and stump hauling, and certainly nothing to grind.

I sold fuller brush door to door at your age.. and that was fun.keep at it.. pretty awesome really your on this site like I said.. you will be fine.