But what about my deduction for this? What about the deduction for that? Hundreds of thousands of pages later, that's how you end up with loopholes that only the savvy/wealthy are able to find.

That's the kind of thinking that led to this mess. Like good developers, we should abstract the tax code to simply define the acceptable conditions for something to be deducted. Then, the Treasury can provide a list of 'standard' deductions somewhere that won't attract any extra scrutiny, and which will suffice for most purposes. Things like a minimum rent amount, minimum food expenses, etc.