Borrowing against your assets might make mathematical sense, but I think it’s kind of stupid to burden yourself with that kind of debt. The tax you pay is your peace of mind and the interest in the loan. Paying taxes on the sale of your investments is simpler, and if you’re living off your assets, you can afford it.

You’re also introducing the risk of being liquidated if there’s a big drawdown in the asset. If you borrow against your stock and then there’s a 50% drawdown, you could easily find yourself worse off than if you had just sold the stock.