FReeper please....
Every wealthy person in history whose wealth was primarily in land/real estate has had issues with liquidity. It's simply a fact and Trump is no different, in fact it's plagued him multiple times in the past.
Trump has cash and marketable securities of around $300 million, that should be enough to get through the primaries, but he will need approximately $1 billion more to get through the election.
So, where does Trump get a billion dollars to self-finance his campaign? Estimates of his ACTUAL net worth are all over the map, but this doesn't matter because he certainly has a net worth in the billions. His problem is liquidating it. Trump has exactly two routes he could take to accomplish this: he could sell property or he could borrow against it and neither option is as simple as it sounds.
Let's say he decides to sell a billion dollars worth of property. How does he do this? Which property does he sell? Does he put everything on the market and see what sells? He needs to find buyers and he has to figure out which properties they want and he has to be willing to give them up. Plus, he would need to face the reality that you drive down the price of property when the buyers know that you NEED to sell it. Finally, there is the issue of timing, real estate often doesn't sell as quickly as you want it to. Could Trump sell enough property to net $1 billion? Sure. Could he sell it soon enough to self-finance once his cash runs out AND at a price he can live with? That's a lot less certain.
Then there's the option of taking loans against his property, but that has its own set of hurdles. This WOULD NOT be a "sweetheart" loan that a bank gives to a celebrity to buy a new beach house, there would be actual underwriting involved and they would want to know how the loan would be paid back. Keep in mind that this WILL NOT be a billionaire borrowing a billion dollars to invest in a business venture that will make money, this will be a billionaire borrowing a billion dollars to SPEND AND NEVER GET BACK. This brings us to Trump's actual income, he would need an income of well over $100 million per year to service the debt. Now, Trump was getting $30 million or so from NBC, but that's gone. He's also earning some money from dividends on his $300 million in securities, but that will be gone too. His disclosures indicate that his REVENUES in 2014 were $362 million, but is that all income? In the case of his resorts and golf courses, it probably isn't. He also has income from the sale of condos in his developments, but that would presumably go away if elected. So, the bottom line is that Trump MIGHT be able to service the debt, but it would be difficult and it would seriously impact his lifestyle for a long time.
So sure, you can say, "FReeper please..." all you want, but what I've laid out are FACTS. The crowds love it when Trump says he can self-finance a campaign, but when you really look at the numbers it's nowhere near as they think. Trump IS NOT in the same position as a lot of other billionaires when it comes to liquidity.