Thanks for the partner recommendation. 

Hi all,Does anybody have any recommendations for architects who are self-certified and specialize in Chicago residential properties including 2 flats (what we have)?

We do exactly what @Bonnie Low is recommending and it works for us.

I would recommend vetting the inquirer first, but yes, we always provide the address under these circumstances.

This will drive how much you can borrow.Consider More Modest Options FirstWith $200k in investments to deploy, look at starting with 1-2 short-term rental properties first to gain experience before scaling up.Explore markets closer to your mom's current location that may have lower costs but still tourism appeal.This allows you to validate the model and your ability to operate short-term rentals successfully before risking more capital.The short-term rental concept could potentially work, but I would recommend starting with a smaller, very well-researched first step to validate the model before going all-in on a larger endeavor.

For those recommending agents, in our experience, +95% of agent only know how to deal with owner-occupied transactions.

Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

Bigger Pockets subscription is recommended, It has a lot of learning material.

Quote from @Kevin SobiloAlso, and sorry for all the questions- for our situation would you recommend consulting with a financial advisor or an accountant?

They were pretty much recommended and handpicked by a contractor I had hired for reno.