The rental properties range from slightly cash flow positive to slightly negative.

Be careful of offers to “modify” your loan, this could affect you negatively on future loans.

For many people after depreciation the amount of taxable income is low or even negative.

Looking at historical stock market returns, you can find multiple 3 year periods in which there was a significant negative return.ROTH IRAs can be a great tool, but I don't think it is the appropriate choice for meeting your goal to start REI in college.

Youth/freedom/time is a HUGE advantage.IN 10 years time, I went from negative networth to 7 figures in real estate and stocks.   

That was just a quick and dirty statistic run, without filtering by rental class type, etc.Some data pulled from the web shows job growth expected to grow at around 37% in the future.

Being a good tenant isn't related to having a Sec 8 voucher and may actually be a negative since rent is mostly (excepting the copay) not the tenant's out-of-pocket money.

I considered the statistics, like the lack of population growth Chicago has recently experienced.  

Just remember: most negative reviews are written by problematic tenants.

No need to be overly negative about positive solutions.