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. 

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

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.

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. 

I tend to hang out in the Tax forum fairly regularly so I may be one of the first ones to see such a thread or post. 

@Devin James ok now you got me "thought vomiting" here but just hang with me a moment cause maybe there will be something. 

hang in there.

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.. 

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