In addition to taxes, the transaction most likely won't be frictionless, there are always accountants, bankers, and government registration fees to deal with, n

In addition to taxes, the transaction most likely won't be frictionless, there are always accountants, bankers, and government registration fees to deal with, not to mention finder's fees. One of the main ways to defer taxes for wealthy people is to borrow against appreciated assets (unrecognized income, not taxable) instead of selling the asset (recognized and taxable). The boat and car in the example are probably not owned free and clear.