Well I'm not there but... I have a small company (corporation). So anything that the business can own is always the business that buys.
In your case I would have a business that invest in properties (and other things). When is time to sell some properties for whatever reason, you sell and use the money in what is more worth it at that time so the company don't pay taxes. You own the company that own all the properties, indirectly you own everything. Everything that the business need and you can use is money that you can choose to be or not to be taxable. And with time the estate grows (the business estate) and you need a private plane to keep up with business. The business buy the plane, but you manage the business, that's why you need the plane. The Business pays fuel, the crew or pilot, all the expenses related to the plane. That help to reduce your company taxes. The plane basically is yours, it's for your use... . To summarize you own "almost" nothing. The business owns everything and you are the most important employee (you or your accountant decide what setup is better for you). You pay taxes from the wages your business pay you or from dividends or any bonus you receive from the business...
@brumasbusiness