Philanthropic capitalism, the sheriff would find, is going to be costly.
Farm 1, being abandoned and ownerless, is much less complicated. Arjay would look into what local land claim procedures were, along with collecting estimates for demolishing and rebuilding the buildings and for the guard postings would be. He'd ask the farmers what they thought the cost would be, labor and all, to bring the fields to a workable condition.
As far as farm 2 was concerned, Arjay would recommend to the council that the land be held by the city until the oldest of the boys reached an age of majority, but to allow their present caretaker to work and profit from the land in the meantime, provided that the boys are well cared for. Working these new fields, he would point out, would increase jobs whether he ran it or this neighbor did so.
Arjay would allow the current situation in farm 3 to remain, and would petition to the city that since the farm is well maintained and contributing to the overall benefit of Shadowdale, both in terms of production and employment, that the currently vacant title to the farm be granted to the farmer running it.
At Farm 4, Arjay would, again, ask for quotes on the rebuilding of the buildings (again modified to the needs of a vineyard and winery in addition to housing). Then he would go to the old man who owned it to propose buying the land with the following concessions:
1) the old man would be allowed to remain in residence if he so wished (Arjay would go in assuming he would want to remain in his home)
2) the boys would be allowed to remain, and would be put to work, either as builders or farmers, so they'd learn some marketable skills to live off of.
To the boys he'd stress that he had no desire to put them out, since they'd cared for the old man through the occupation (presumably) which spoke to good character, but that theft had to stop. Should the land purchase fall through, he'd talk to the neighboring farmers about giving the boys work to cover what they needed.