Some of the materials we choose and asked him to pick up (such as flooring) he replaced with low quality materials, I assume to keep more of our money for himself. 

Target Low Vacancy RatesChicago neighborhoods like Lakeview and West Town boast low vacancy rates, meaning fewer empty months.

Meet with a local banker & schedule a time to talk with a mortgage broker, they'll give you at least a baseline of what kind of down payment options and rates are out there.After that, if you're still wanting to research more creative options, do some looking into seller financing (a very hot topic with good, and bad, advice out there), look into private lenders, and commercial financing options.If you're wanting to live in 1/4 of your quadplex, then conventional residential loans may in fact be your best option as you can purchase that with a fannie/freddy loan with very low down, and use up to 75% of the income from the property toward your own income. 

If I ever run low on reserves, I can easily transfer funds from my personal to rental account.

Set up a contracts account at both Lowes and HD. 

Nicholas makes a great point—having strong ties to a market definitely helps, and picking a random low-cost market without a network can be tough.

Low prices enable more people to buy, limiting demand for rental properties so rents decline (in inflation-adjusted dollars).Population Growth: In areas with growing populations, demand outpaces supply, driving up property prices.

As you can tell marine the appraisal came back 40k low and I was so dumbfounded.  

But also with low debt or free and clear property that they can easily access any time in the future with a cash out refinance.

Personally I like keeping my properties that I know are successful and have low maintenance.