Good points. I think he was/is running some kind of a scheme (since JD filed for divorce in 2017) that provided a cover for claiming poverty and not being able to pay back his FIL, pay subcontractors, or pay for divorce attorneys.
Or he was/is terrible at his job, and only ever limped along when graciously and fully funded by his wife's family.
Or he was/is a grifter who thought if he just kept on doing what he had been doing (building high priced mansions in wealthy neighborhoods), he could keep up pretenses that he was still a successful builder, there was still cash flow, he could take some big writeoffs at tax time, get more clients who liked what they saw, wait for the market to rebound, and in the mean time do everything he could to keep JD from divorcing him and his in laws from collecting any money he owed them. Or declare bankruptcy, and wash his hands of the whole stockpile of mansions that wouldn't sell 'due to the market'.
Just the property taxes alone on multi-million dollar properties would be astronomical. But maybe lower if unoccupied or unfinished???
It could be way more complicated than that -- sounds like GF's attorneys are going to dig into his accounts any day now, and MT will be questioned as well. One more way in which he was probably up to no good. MOO