They are property owners in your neighborhood, not an external company with no stake in the community other than management fees. 

You're being asked to pay $3000 to learn lending from a man that has zero formal credit background, lost his professional license in AZ, and who didn't even get into real estate until 2011...so he's never been through a downturn.

My credit card companies will direct deposit the cash into my bank account in a day or two upon request.

We shoot for young working professionals, or grad students

@Tabitha KixSSBA has a decent amount of properties, but they are just ONE Brokerage Company among approximately a dozen that specialize in Storage.

Because of my professional experience, we'd prefer that our properties be nearby so we can self-manage and save the 5-8% typical of property management fees, at least until our portfolio grows.

I am an IT professional wanting to start investing in real estate.I am based in Chicagoland.

Is it legal to do an off-market transaction straight through the title company without using the agent? 

There are companies/agents that specialize in what you are looking for.  

I just recently found out that my company is closing mid summer.