If you compare the results of investing in a taxable account vs tax-deferred in just 15 years the difference will be huge (hundreds of thousands $$$).

You may have some deductions that could mitigate the taxes if you are buying income producing property.

The deals I’ve sold over in that direction this past year, are the ones I am most excited to see the result of. 

There are definitely places to buy that currently produce a decent cap for rentals outside of the marine bases.

Maybe look at fix and flips as way to produce more income in addition to what your rentals produce.Also, keep in mind that most real estate agents are paid by 1099 and are commission only.

One of the worst situations that could result is that the contractor does not get paid and they go to the courthouse to place a lien on your property. 

We have high income, low income, areas of great appreciate, areas of great income producing, section 8, high rent condos, middle class suburban....it all depends on your goals and budget.Second, I didn't say you couldn't trust comps in Chicago, I said you couldn't trust them in the neighborhood you are looking.Third, there is no substitute for going to the area you are going to invest hundreds of thousands of dollars. 

Pick the applicant with the better report results.

maybe do some reading about Detroit and a few other rust belt cities that are tackling this with good results.

But I will commit to this business model and see the results for myself.