> then I would have to file much more complicated taxes and therefor get much less enjoyment from taxes being easy for personal income. Still by not doing so I

> then I would have to file much more complicated taxes and therefor get much less enjoyment from taxes being easy for personal income. Still by not doing so I am giving up tens of thousands of dollars a year. For tens of thousands of dollars per year, surely some tax/company admin service exists that could offload the vast majority of the tedium from you, leaving you with perhaps 10-20 hours of effort/personal attention per year. Even if they take half of the $20+K savings as their fee, that leaves you with $10+K to put in your pocket for a little over a day of total effort. That's $500-$1000 or more per hour of effort (all tax-free). That seems like a huge overlay for you.