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

It should be evident that so far he led me to ask questions how to be in legal compliance while following his model, rather than jump off the cliff blindfolded, believing that the "deals" are hanging all over the trees down the abyss, waiting for me to pick. 2.

They can't wait to hang the hammocks. 

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.

It gets into the furniture and permeates each room they hang out in.

If you can hang on till Spring, @Brian Burke's book on how to vet a syndicator should be published by BP.  

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

Invest in different asset classes, sectors, geographies, operators, funds...a little bit everywhere until you start to get the hang of how to actually look at 'good' deals. 

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

hang in there.