I'm looking to get away from my hometown in O'Fallon, IL, for a week or so and stay with a family that invests in real estate or owns a business and uses it as a business write-off and to be a sponge and learn some information from wiser individuals.

Maybe your desire to make money is hindering your ability to objectively see what's available.

I'd rather not do two individual replacements with the timing working out perfectly. 

Find a bank that is savvy with self-employed individuals. 

Looking into it, I see most hard money lenders will only lend to LLC's or other corporations, and not to individuals.

Here's from an old blog post i wrote -4 Tips for a Value Reconsideration RequestLook for objective factual errors in appraisal report.

They want it to be a "meaningful" amount to each individual.

Products - and your rental is a product - are priced based on all kinds of factors, including scarcity, business objectives, long-term strategies, etc.

I have worked with several individuals that try to broaden their net by selecting multiple markets.

For example, most 4-plexs for individually metered electricity and gas therefore the tenant pays for them, however the owner still covers water/sewer/trash which can be a couple hundred dollars per month depending on the area.