If there are comparable properties at $2,500, $2,100, and $2,000 then we might choose $2,300 or $2,200. 

My copy would be a lot different speaking to another company compared to speaking to a regular consumer who looking for a service.

I would be all in for 1.42 mil give or take and he would be in for about 2.1ish mil with expected appraisal of about 3.6-4 mil from comparable businesses.Expected monthly income of about 40k with 15-17k for the note and would do a 60-40 split on the remainder.

Your finishes (due to ARV) will influence directly your cost, so the full gut price in upcoming areas will be lower if compared to a similar place located in a more "established" neighborhood. 2.

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.