Because of a part-time job in Chicago (housing reimbursed by employer)  I'm considering an investment property in the area -- if for no other reason than to write off expenses, and because there are still deals to be had here. 

This may sound like an emotional call, but I've always wanted a high-rise condo with a view of the lake and the city. Honestly there aren't a lot of other good reasons to live in Chicago ;)

I've been underwhelmed by the cap rate on standard rentals, but noticed this analysis of airbnb rentals:

In short, Chicago is the 3rd best market in the country, with a 71% occupancy rate. Looking at comp rentals, it looks like I could get cap rates of 10-12% at least. 

What makes me hesitant is:

- I hate HOA's.

- The market for non-HOA properties (including dilapidated multi-family shacks that look terrible but must cash-flow like mad) has skyrocketed in the past 4 years, whereas the market for mid/high-end condos with HOA's is still pretty bad.

Questions for people doing this:

- how much work is it, relative to a regular rental? What sort of property management / cleaning services do you use?

- would this at all be feasible for a mostly absentee landlord (albeit, one with family in the area)

- for properties with HOA's (i.e., most of the ones in high rises with great views), are you cash-flow-positive?

- is there a sweet spot that minimizes vacancy? Downtown/streeterville? South loop? Lakeview, Edgewater?
- I've noticed people listing their units on airbnb in buildings that officially prohibit it. Is this a gray area? What are the repercussions if you're caught?

Thanks for your perspectives.