3. Unless you are world-renowned, no one is going to buy it back from you
When you buy a sports car and decide to sell it back because you want to get a better one, that won’t be a problem. If you take care of it well and at least maintain its value, you may even get a good deal. But when it comes to private jet, that does not apply.
Yes, a classic aircraft can have increasing value than its purchase price. But that takes decades of maintenance. You know it well by now that maintaining a plane costs so much more. So, unless you are planning to take care of your private jet for years until it can be categorized as classic, this scenario is not going to happen.
Some celebrities and billionaires successfully sold their private jets because their names speak for themselves. Unfortunately, moderate rich people do not have that privilege. So, your jet will end up on the ordinary used-jet-for-sale list.
In the end, you will end up spending more and more money for maintenance costs or selling your jet cheap. Either way, you will lose even more money. The question is: Is the luxury worth all the trouble?