When you are registered to multiple companies, have trusts, and various taxable investments, you better know your tax code. And guess what? Most 99% of Americans aren't well versed in tax code, especially not entertainers and athletes that spend 99% of their time working on their craft, not trying to find obscure tax loopholes and filing assloads of extensions to beat back the IRS.
There's no software guiding you through that stuff. There's a reason why accounting associations and certifications ie CPA exist.
As far as money management, you do you. But when you're managing millions of dollars coming in from various places while you're trying to do your job, its very hard to make the right decisions and do it quickly.
Best thing you can do is find someone you trust, then sit down at the end of the fiscal year and review the work yourself or have a 3rd party review the work. Every year.
