Second, I would actually argue that everybody being unhappy with the tax system is an expression of the too complicated tax system. The problem is, that everybody has the feeling that their neighbor is paying less than their fair share, because the neighbor has found the one weird trick to avoid taxes. So I would actually argue that the opposite is the way forward, radically simplify the tax system, say you get some tax free minimal income and everything above is taxed with 50%. Then people would at least have the assurance that they understand how taxation works, and I would assume are quite a bit happier paying taxes. (Well, nobody likes to pay taxes, but at least compared to now.)
Taxing money at the point where it leaves the 'corporate' sphere and enters the 'private' sphere is also a fairly simple way of ensuring there are no loopholes. This is also why tax on capital gains is necessary.
Deductions take them in the other direction, giving people with higher bracket income a larger benefit than people in lower tax brackets. Of course they are still paying more tax, but deducting $30,000 of mortgage interest from the 39.6% bracket is quite a bigger tax benefit than deducting $5,000 of mortgage interest from the 20% bracket.
A company's rent for their office space is considered a business expense. That's what I'm proposing for individuals. Each person is an individual "business" selling their services on the open market. Every expense that is necessary for them to be able to do that should be deductible.
Yes, it would make people's taxes more complicated, but also much lower. Software like Mint and Personal Capital already make it easy to track expenses. Although they might not be accessible to everyone, such as people who are unbanked, but in that case they're probably not making enough to be taxed in the first place.