I would look at Facebook and instagram adds for your specific area.

Tell us what you really think of the opportunity and ask more specific questions.

Plus, very important to understand the new layout and how the dig down will effect the existing stairs, plumbing, etc.Happy to connect and talk through your specific situation because @Bruce Woodruff mentioned every project is different and know one price fits all espeically with these complex jobs.Where at in Chicago is your building?

Hi Joshua,It really depends on your situation and your specific needs/wants.

You wrote commercial, but then talked about offices specifically. 

Nore the rent control bullet is CA specific and I do not know how ADUs affect rent control in other jurisdictions. 

Hi Linda,Lots of great advice from @Carla Gordon @Brian Schroeder @Jay Thomas Specifically I think it's always smart to check out FF Traveler sear https://www.furnishedfinder.com/housing/New-York/New-York) and Airbnb/VRBO for 30+ days stays to gauge what sort of similar properties are currently out there!

•HOA & City Rules: Some areas have restrictions on STRs, so always confirm whether short-term rentals are allowed in the specific community you’re looking at.7.

Happy to share more specific ideas!

For CO specifically, are these year-round (Denver metro and Colorado Springs) or resort/seasonal for skiing (understanding Colorado mountain summers are still glorious).