Regarding appreciation, you are right that appreciation by itself would be speculation, but i believe that since farmland is a commodity producing asset that appreciation will be driven mostly by global population growth and not directly housing/local population growth.I'm not too familiar with the cash on cash returns yet but let's say the land is cashflow negative after tax/mortgage, is there a way to know if the deal is still attractive?

You are choosing the road less traveled and there are challenges as a result.

It can be mathematically shown that on average there is no place in the Midwest that on average has produced a better ROI for financed buy and hold RE than San Francisco, San Diego, Los Angeles for 5 years, 15 years, 20 years, 30 years, 40 years, 50 years.    

I believe it would be very difficult for me to separate myself from direct liability from issues resulting from the property, as I am a direct manager of the property (it's almost absurd to think that I will never perform any managerial tasks or be responsible for the same as a live-in owner-occupant).

I added to my list and After about 3 months I saw results.

The result has been refi appraisals that are at $80,000 each, i get $850/ month rental and I get very good renters.Your on the right path by doing it right.

@Jake K. the results from the Baltimore city tax sale area at bid baltimore.com or you can buy the list from the city municipal building.

Assuming the borrower actually completes the BK, the result is that the borrower no longer has a Personal obligation for the actual debt....the mortgage against the property is not affected in any way. 

@Reid McKay Knight I completely agree with @Mike Dymski  People invest in other people that have experience, proven record, transparency and consistent results.

that is the long term plan, is to have a holding company (LLC or C-Corp) with the rest of LLCs under it as non income producing LLCs.