But one thing I see is when your ready to hang it up one better have ZERO debt .I once asked a bizz partner of mine when he thought he could stop his day job.. 

I'm great at reading people - that comes with playing millions of poker hands in my life - if my gut tells me things do not sound right then I pull away.But a scammer has to expose himself/herself because they don't wanna hang around forever.

I work in WA, not IL.Sounds like similar facts - you need to be licensed if you are going to manage other folks' property.Here, you need to hang your license under a managing broker until you can get your managing brokers license, as brokers can't touch money and do a few other things legally.If it's like WA, you will have to hang your license under a managing broker at a brokerage, and coordinate deposits, contracts, fees with them.If that is the case, ask some brokerages that will allow you to hang your license under them for minimal fees in order to be compliant.

How he was barely hanging on and wasnt getting paid any of the money I was sending the GC.

hang in there.

As for AirBnb itself - they are far easier to work with and get the hang up than VRBO. 

You will also need wall hangings and art, not to mention kitchen stuff like silverware, pots and pans,

Stop hanging out with your deadbeat buddies who spend all day drinking, talking sports, and otherwise wasting away.

I do appreciate a cheaper entry point, so that I can afford to buy more doors, without putting all my eggs in 1 or 2 baskets.. 

Thought about adding a hoarding clause... one of our tenants has a side hustle where they buy, build, and sell holiday gift baskets.