So I poked around and this is what I found for his financial and legal situation. Figured most of the people in this community would get a kick out of this.
His loans look something like this:
162 million to the 'Vornado Partnership' due 2021 against a hotel in San Francisco
285 million to the 'Vornado partnership' due 2022 against a hotel in New York City
100 million to the bond market due 2022 against a New York city property
340 million to Deutsche bank from Germany due between 2023 and 2024 against multiple golf courses and hotels, and they can come after Trump's personal assets
13 million to the bond market due 2024 against a few New York city propertys
Thats 900 million in loans going to get called in over the next few years with 5 or 6 other loans that were a couple million each I didn't mention. Trumps tax records reflect his property's are not producing enough cash to pay back their loans with business slowing from his public image issues as well as the pandemic. His hotel empire reported an average occupancy of 23% last year.
All this is further complicated by the New York attorney general investigating him for fraudulently overstating his assets to get business loans which will greatly hurt his ability to get loans right now and his largest lender the Deutsche bank (which he has done business sense the 1990s) has voiced that they will cut ties with him removing his ability to refinance.
On the legal side things look just as bad:
Its widely speculated the IRS may come after him for tax evasion for a process known as 'Debt parking' where he loaned 50 million personally from Chicago Unit Acquisition LLC which is a company he owns allowing the company to operate at a loss for the year.
Then there's the New York attorney general fraud ongoing investigation I mentioned earlier.
Also the Manhattan district attorney has been issuing subpoenas and questioning witnesses before a grand jury while fighting to the supreme court to obtain corporate documents and tax records to lay the ground work for a wide variety of charges related to Trumps financing and insurance interests.
The hush-payments thing is still ongoing although the only provable thing is that Trump has falsified business records.
There are 3 separate ongoing lawsuits that allege failure to seek the consent of Congress before accepting any benefits from foreign states in various ways.
Then there are some ongoing sexual misconduct lawsuits including one by 'Jean Carroll' which will result in some variety of sexual assault if Trumps DNA is matched to the dress she was wearing at the time of the assault.
Then theres the issue of Mary Trump vs Donald Trump that claims he and his sons siphoned money away from her inheritance when they were tasked with looking after them (because she was under age when she inherited them.)
All of this is to say- Trump has a very dark few years coming his way where he could loose his business empire, his personal assets and his freedom. All that without even touching on what happens if the fed decides to go after his illegal actions during his time in office. Historically he has been creative sourcing money but that may not be possible this time around. He will probably have to do some really shady stuff under the table to stay afloat.