Buy Luxury apartment in download for AirBnb

[Han W.]

Hey BPs, 

I am considering to buy a nice apartment with magnificent view to start my first Airbnb. I am still petty new to this area and would like to hear more suggestions about potential pros and cons I may have in future. 

My current location is Chicago city and target for 1b1b or 2b1b. However, after browsing many apartments on sale, I have two questions and hopefully someone familiar with market could help me to understand this. 

1. The price of many downtown apartments have been decreasing in recent 5 years. I guess that maybe due to the high HOA? Will this be the normal case for property in bigger city like New York or Los Angles ? Does this mean it will be a bad investment in future?  

2. I hear that many apartments' HOA do not allow to run Airbnb in the building, it may be more risky to buy it. But I do see many properties listed from Airbnb, is that possible to avoid doorman for a longer term and how do people handle self-checkin in residential building ?

Please forgive me if I ask stupid questions :)  Thanks !