If you're up to training and caring for an animal, a dog is an excellent deterrent against unwanted strangers and intruders. 

I nodded along with much of it and you helped me visualize actions I had been pondering.

The cost of transactions and the increase in property taxes is also a deterrent. 

If it's a good deal, moving out a previous tenant's leftover furniture shouldn't be much of a deterrent to you. 

If so, do you find it to be a deterrent for many buyers when you try to sell it after the flip?

I am impressed with the visual transformation of the house.

Vacancy rates will rise quickly.Maybe you could try an Iron A/C cage on the outside and a separate security deposit (maybe around $300 or so) to cover the A/C.The cages are ugly, but in many window A/C communities the residents understand that their neighbors (and their neighbors visitors) may be, shall we say sometimes "theft prone", and the bars can be explained as break in deterrents to keep their belongings safe.They also blend in better in a light color vs. black.If a prospect balks at the $300 and you want them, you could always offer to wrap it into the first 10 month of payments.

I'm also interested in buy and hold on farmland.I have an academic background in GIS (custom mapping and data visualization), and I do some of that freelance, including setting up a pretty impressive crime watch program with a HOA in the area.  

I suspect most people on here consider 'beaters' to be perfectly fine mechanically, mostly visually OK vehicles with some flaws that are reasonably comfortable and serve the purpose without costing an obscene amount of money.

If you love diversity, love music, love visual arts, try NYC.