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-processes

Yes, I had always heard that it could be hard to finance a property outright with an LLC, so I'd always assumed it would have to be done in an individual's name first and then transferred to an LLC afterwards.

Is it individuals or companies?

Find out is Indiana allows eviction for possessiona and document all the lease violations and hire an experienced eviction attorney.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-processes

If you choose to finish the space later, the paint doesn't need to be removed, so no harm.

If none of that was done, you just made a $50 voluntary donation to someone....I suspect it will be a matter of time until the individual that received your "donation" receives a visit from the FBI for wire fraud. 

These costs for most of the individuals are considered personal in nature( unless you have RE portfolio that is run like a business- see below).

I am new investor in Chicago looking to connect with other like minded individuals.

I'm selling them individually and have the first contract. 

Knowing it could be re rented with zero vacancy so what is the harm.