AirBnB Short Term vs. Long Term in Chicago

[Eric La Pratt]

I have a multi-unit in a class A neighborhood in Chicago (Lincoln Square - 60625) that I am wrapping up a large rehab on right now. The property is on a remarkable block and the units really are fantastic - we've taken great care in choosing finishes and upgrading many items. The last 2 units are coming online right now and we're suddenly considering AirBnB vs. long term rental. Here's why:

An old friend of mine from the hospitality world has cofounded what I understand is the only "full-service" short-term rental property management company in Chicago and they manage over 100 units - doing everything from price adjusting to marketing to filling to cleaning. I do not believe they are paying your utility bills or ordering maintenance but they are cleaning and turning the property over day after day if necessary. They charge a 29% fee to do this - literally answering every email/message, writing feedback, acting as a concierge services, meeting tenants if necessary (normally doing lockbox/coded entry nowadays), etc.

The numbers his company prepared for me are almost too irresistible. We're talking netting roughly 50% more than I would net with long term tenants. I've run their same numbers considering if I were to property manage it myself, and the numbers are staggering. All said, I have a few detailed questions:

1. Does anyone have experience in running numbers for short term rentals that they can share how to do it?
2. For those of you who are doing this, how are you furnishing your units? How do you figure these costs? Do you rent? Buy? I would think that we would want our furnishings to similarly match the beautiful finishes we used (wherever that sweet spot is) in order to maximize our returns.
3. How are you managing the turnover/cleaning? If you do it, how do you arrange for when you are out of town?

This is a good start to hopefully getting me to a space where I can make an informed choice.