Running the numbers on STRs in Chicago, it seems like there is an opportunity to generate strong cashflow with minimal upfront investment by using this strategy, but I'm curious if anyone has on-the-ground experience with this type of model.  

Right now Facebook is dirt cheap compared to Adwords, however not for long.Here's the thing Facebook ads is a push type of marketing, whereas Adwords is a pull form of marketing.

@Joe Graziano I’m definitely a multi unit guy, i can see the scalability and advantages compared to sfh.

There are not many properties for sale and the ones that are seen to be highly priced compared to the rents.

They all should be able to provide you a CMA (Comparative Market Analysis).  

I'm really trying to get my real estate investing  career off the ground. 

Probably not with a traditional turnkey provider who offers you the final product at a premium price, as many mentioned here already.I built my property management business by basically offering our service at a fixed cost, being the boots on the ground for the out of state or out of country investor.The basic approach is, you find a good local team that will find you the distressed property, rehab it for you, rent it for you, manage it for for you.

@Jay BedsworthThere are some advantages to the Solo 401(k) as compared to a comparable IRA. 

You can easily get a 60K foot view of a market by studying readily available economic and demographic trends but to really know the ground level nuances you need to spend some time in the market.

Donna Bauer has a great cours that is peanuts compared to what the expensive gurus charge and it will explain notes very well, as does Papersource University Online, good solid low cost education.Buying a performing note at the lowest price you can get it for is a good start on FCI, as they can service it for you and there is little work other than get paid back, unless they stop paying.