Wow! What a cool looking property! Definitely worth thinking about!
The thing about 'unkemptness'... When you are homesteading, there are constantly a barrage of projects to work on. That fence needs repaired, the goats' hooves need trimmed, the toilet unclogged, oh crap, the hinge on that gate needs fixed!, the rocks need taked out of the garden and the garden tilled, etc. The list is endless. Once you finish one thing, two more pop up.
Things tend to get put aside 'for later'. Some brush needs burned, a piece of machinery fixed or sold, some old fencing laid aside for a future pen, etc. It is super easy for all that to get away from you.

Excited to see which property you end up choosing!