Just on your first one...
Trump acquired a chunk of 1290 Avenue of the Americas almost by accident, when Hong Kong investors who’d bailed him out of a residential project near Lincoln Center swapped it for the midtown office building instead — leaving Trump with a 30 percent stake in the office building that is locked up until 2044 — which means he can’t sell it until then.
The government could lien against (i.e. Trump gets a loan against its value and income from the building goes against repayments) the building. Trump would be in a very poor place to negotiate rates, he has a history of lying to lending institutions and over valuing properties...
I say James will go for Trump's 100% owned assets first, ideally debt free and in NY... These could be Bedminister, Golf Courses, Mar a largo (is also a possibility)... James will cherry pick what is easiest to pick off the bones and get the NY State their money...
Let's be clear, Trump was clearly known that this kind of judgement was coming down the line for a few years.. Well that is his lawyers told him the truth. He didn't prepare for this when he had options... He could leveraged properties last Sept when he effectively lost this case...
He acted like a idiot in business sense. When he should have been liquidating assets and having money available, finding top class lawyer and listening to them, he hired bargain basement lawyers and acted like a jackass in court. His lawyers were so poor that they gave Trump very few places to appeal.
Trump could have got away with this if he was a bit smarter... He first shouldn't have thrown Cohen under the bus, that was the first problem. Get good lawyers and pay them... This fine could have been less than $100m if he knew how to plea this out.. Trump did the exact opposite and that is when the big guns are brought out... Trump is now backed into a corner and himself and his lawyers got them boxed in with little legal challenges on appeal... Example: the low valuation on Mara largo wasn't challenged in court in a timely manner (i.e. during the initial case(I believe)). This means cannot be brought up on appeal.
Because Trump didn't prepare for this judgement. James is going to chery pick his properties and have a fire sale. There is a lot of real estate guys looking at bargains and James will be selling at knock down prices to get NY State their money. That is how it works and it is no different for Trump.