But is it really worth that much time and energy to get that

extra $20000, or $40000 in investment income when you can easily make that amount at work in 2 to 3 weeks , with guarantee. To have good invest return, you need to spend time on it, period. Otherwise , it is easier to loose than to gain. My advice, buy the best long term disability insurance you can get. So you have protection of your earning ability.