So the good news is that there are currently two full-amenity condo buildings in/near downtown Chicago in prime A+ Class neighborhoods that allow short-term rentals: 545 N Dearborn and 30 E Huron.

., "East Basin", or “E-Basin”) separately if required by the system.

I still continue to use another e-signature solution (can use it for other things other than lease management) but may try e-signature options for leases.

But how do the suspended losses for final K-1 flow into Schedule E line 41 (or line 32): from line 28 column g (passive loss allowed via 8582) or from line 28 column i (non passive loss allowed)?

Typically each partner would just report their share of the income and expenses on schedule E. 

If you are reporting it on a schedule E (you are not taxed as a corporation or as a partnership in non-community property states) then no, there is nowhere on your tax return that shows your cost basis and your tax preparer likely doesn't know. 

Unlike e-commerce or social media platforms, where data privacy issues are more visible, the real estate sector often operates behind the scenes in this space.

Having just been licensed in MA, I've been looking for local meetups and investor events and I've found this one so far, a real estate investors networking dinner in Downton Boston on 10/15: https://www.eventbrite.com/e/boston-real-estate-investor-net...The event is free and I've registered for 2 tickets for my partner and I.

I would ask for the last few years of the Tax Return Schedule E for this property to see what their total expenses and net profit was.

Quote from @Derrick E.: My free advice, don’t pay for some real estate investing course.