@Nick OttenbacherI have done a conventional cash out refinance with a similar type of property, prior to taking it through the subdivision process and selling them individually.

If you are 19, you have a few more years to go before you graduate and once you do, you can rent out the entire house instead of individual rooms.

Tar / patching depends on what is around it and is only a band aid. 

I’m listing it as an individual, not via a property manager. 

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.

You've got to give them notice and rip the band-aid.