Hey @Brie Schmidt :)
I've followed your opinion on condo's and had been looking forward to discussing. There are inherent risks you'll need to understand that come along with investing in any type of property. My experience with condo associations comes from managing 23 different associations in Chicago and from purchasing 4 separate units this year. I don't think of HOA fees as an unnecessary expense but as forced savings for inevitable repairs that need to be made to any building. There can certainly be mismanagement of the reserves so you might have to join the board of your condo association to make sure lenders approve of the health. But across the properties I've purchased the expense ratio is only 35% and that is including a conservative budget of $100/month for repairs on each unit.
I share your concern for the inventory in Chicago and its potential for rents downtown high rises, but feel comfortable that rents won't drop in a lot of other areas.
Want to continue the discussion but am running late for a flight! Happy Thanksgiving everyone!