That way I have multiple reasons for people to visit the area.Great locations:On water, ocean, lake, riverIn the mountains Close to amusement parks such as Disney. 

You will likely have to look closer to O'Hare (Schiller Park, Elmwood Park, River Grove)  or maybe a bit further East in areas of Chicago along the blue line like Jefferson Park.

Even if you hire a professional, established, local company that manages vacation rentals, you'll probably still make more than if you hired this other company that solicited you out of the blue.

So if you MUST have ocean view, PCB would be the lowest per sq ft right now. 

Transit really helps on the long-term appreciation side.I tend to agree with you regarding Back of the Yards having less appreciation compared to those off the blue line that you mentioned above. 

Now, instead of 50 shades of brown throughout the community, our house is a nice blue color!

The Pt loma unit is ~5 blocks from the ocean and ~5 blocks from the bay.I really do not know what a $4m property would bring in as an STR, but 2 of our STR units are a duplex in Mission Beach that is worth ~$1.6M. 

Their starting price is most likely their blue sky want, not their bottom.

Next up, think of a blue elephant!

Getting a 70% of ARV - repairs deal here is becoming as unicornish as the rest of the nation I’m sure, but every once in a blue moon they can be had either with strong sourcing efforts or negotiation tactics - which I’ve helped my clients do from the MLS.