Luxury condos. How dumb are they?

[Tyler D.]

I want to buy a waterfront condo in Chicago. The idea seems very sexy, and maybe profitable, but I'm not sure if it makes the most sense financially  As I see it, the pros and cons are:

Cons: 

Likely won't cash flow in the beginning. 

Doesn't come with land like an SFH.

Id be subject to an HOA that can change policy/ raise fees at any time.

Pros:

Waterfront space is a scarce resource which could lead to better long term appreciation. (I don't need immediate cash flow and care more about total long term returns).

Relatively affordable compared to other large cities (though the same is true for  SFHs). 

Likely easy to manage and low vacancy due to being an A class area.

It's a cool place that I would like to stay/ visit. Being a scarce resource, opportunities like this may not exist in the future, or may get priced out.

Due to the recent fleeing from cities, not might be the right time to buy a condo, instead of houses which have shot up in price.

Your thoughts?