Trustless automatic collection is the best way to equalize the tax system. The technology to collect taxes on investment income as someone generates it exists right now. Blockchain software constructions called Smart Contracts; or decentralized apps (Dapps), can be built into financial instruments like stocks, bonds, annuities, derivatives, and cryptocurrencies.
The Smart Contracts, or Dapps, can be programmed to pay the Treasury a percentage of the funds generated as taxes. For example, a stock Dapp, would pay a percentage of dividends to the Treasury.
Trustless means that nobody needs to trust that people will pay their taxes. Algorithms automatically collect the taxes before the taxpayer gets the money. Most people do not think about sales or withholding tax because they never see the funds.
Trustless taxes discourage tax evasion because there are few opportunities to evade them. Most people cannot evade trustless taxes because they get no chance to do so. Many taxpayers will never even think about trustless taxes which reduces the incentive for evasion.