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.

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.

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

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.

We don’t know anyone in the area, but you might want to read our series about “How to Screen a PMC Better than a Tenant”, since selecting the wrong PMC is usually more harmful than selecting a bad tenant: https://www.biggerpockets.com/member-blogs/3094/91877-how-to-screen-a-pmc-better-than-a-tenant-part-1-services-and-processesAdditionally, don't treat property management like a commodity and just focus on the lowest price!

We don’t know anyone in the area, but you might want to read our series about “How to Screen a PMC Better than a Tenant”, since selecting the wrong PMC is usually more harmful than selecting a bad tenant: https://www.biggerpockets.com/member-blogs/3094/91877-how-to-screen-a-pmc-better-than-a-tenant-part-1-services-and-processesAdditionally, don't treat property management like a commodity and just focus on the lowest price!

I am currently working towards buying ownership into an office building structured with an association of individual owners for the individual units.