What’s wrong/right with taxing net worth?

How do you determine net worth when the value of many things is constantly changes or may require and expert to appraise?

If I own a lot of stuff, but don’t have a lot of cash, is the expectation that I’ll have to sell stuff to meet my tax obligations.

Can I just carry a ton of pointless debt to make my effective net worth $0?

It would be messy. It’s not impossible, but it would be messy.