Coaching – I’ve been coaching ever since I was in college and I love it. And since I coach a club team, the time commitment averages only about 10 hours a week. The money isn’t great if you depend on it for living but it’s the perfect secondary source of income since it’s very easy for me to get hired as a coach(and it’s tax free through business deductions).

Since David may never be coming back to this site, If anyone other than David can point me in the right direction, Id greatly appreciate it. I live in Chicago, and I need to buy a quality rental to hold long term somewhere but I have no idea where, and I really don’t want to buy in Chicago. Chicago is insanely corrupt and in HUGE debt. I cant leave Chicago in the near term, I take care of an aging parent, and if I left, my salary would drop by 50%. Id still like to diversify into a rental property.. but I feel that if I just call up a stranger, they’d attempt to sell me their best pig with lipstick, and pressure me to jump on the deal before someone else ‘stole’ it. I have no problem hiring a property inspector from a different city, but don’t want to waste hundreds of dollars if the agent is steering us towards crap property after crap property. I’m looking for broad advice. Any constructive reply appreciated. Thanks guys.

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In focusing on your wealth management goals, investment income is obviously critical but you might fund your goals from wider sources of income.  A typical long-term portfolio might produce about half its return as income and the other half as capital growth, though in times of duress the capital growth component wanes.  In this low-interest rate climate, some sources of income have become quite expensive and may prove disappointing against your spending needs.  But by tax efficiently and sustainably drawing income from wider sources, you might meet your goals while more prudently balancing risk against reward.