I can imagine several issues, but is hackernews the right forum to discuss tax reform? You can either go the respectable economic modelling route and be prepare

I can imagine several issues, but is hackernews the right forum to discuss tax reform? You can either go the respectable economic modelling route and be prepared to do a lot of work to justify it or perhaps try a tea-party forum where simplistic tax gets kicked around all the time. Tax is complex because the more complex it is, the harder it is for people to reason and try to work around it. A good tax system is like a secure computer, with defense practised in depth. You might breach one layer but another will catch you. Another issue is wealth is something that is difficult to assess and can cause severe disruption. Say for example you are a FB employee and get a nice asset boost in an IPO. You get a big tax bill, but your shares haven't vested. Now you owe the tax office a whole lot of money that you are unable to raise. By the time your shares vest, they might be worth a fraction of the tax bill. How about if you start a business. You earn enough to feed your family and suddenly, your "business" is an asset which could be sold, so you get taxed on wealth you are now purported to hold. Is the tax office going to require you to assess how much your business is worth? What if they disagreed with you? You have a family home and its worth has gone up in a property boom. Now you have to pay 4% of the market value, but when the boom is over, you have been out of pocket of those extra amount without enjoying any benefit of it.