I did a fair bit of research on the Duggar properties a couple of years ago, and Jimbob almost always buys for the land itself, usually foreclosed properties or sometimes heavily discounted properties, rarely improves them, and usually sells for significant profit years later. He’s a speculator not a landlord.
He’s definitely not poor.
The giant house he’s selling is at the top of a large hill, at the end of a road. I’m not sure it was just a single residence when Jimbob bought it, because it had “no alcohol beyond this point” signs and emergency exits and such when we saw Jessa visit the place. It had a rotting indoor pool in the middle .