We need more supply to do that.

Just be mindful of the demands and challenges it entails.Best of luck with your venture!

Some STR hosts have switched to MTR though with the laws so maybe you just have a supply problem there.

I get it.. for homeowners this is a no brainier for apartment dwellers this is still going to be a challenge going forward. 

Each unit is individually owned, with some owners holding multiple units.A few things I’m trying to understand better:Pros and Cons: What are the main benefits and challenges of owning multiple units in a property like this with a condo setup?

Starting small and scaling up is a tried-and-true path, and this community is filled with people who’ve walked that road and are eager to share their experiences.Feel free to ask questions, share your wins (and challenges), and tap into the collective knowledge here.

Challenges?

Depending on where you are looking, inventory for 1-4 units can be a challenge as a lot of the NW suburbs are all single family homes unless you are further NW like Rockford or Elgin or something like that. 

These are similar softwares that hotels use to constantly change pricing depending on the demand/supply for the area. 

It's challenging to find lenders that are willing to be in 2nd position on an investment property, but I called quite a few during the process.