I don’t have funds for a condo down payment unless we sell the other property to free up cash.My dilemma is whether to keep the house and wait for the market to reach $2 million, go back and live in it, or explore other options.

Just don't pay anyone a nickle, a real mentor would help you for free. 

Excel is cheap and Google sheets is free.

I'm also curious about how investors are navigating this high-interest, low supply market.Feel free to share your insights, predictions, or even any cautionary tales, etc.Thanks in advance!

Just sent you an invite to connect feel free to message me

But I will utilize this recovery time to gain as much knowledge as I can.I have a plan in place to be debt-free in the next 6 years so I know that will help as well. 

I told them I'd rather just help them for free via email with the occasional questions.That was 1000 emails ago.  

Here's the City link for you to reference. https://www.chicago.gov/city/en/depts/doh/provdrs/homeowners...1) ADU regulations specifically exclude Short-Term Rentals so don't do it if the intention is to short-term rental. 2) The ceiling height oh 6'10" is almost guaranteed to trigger digging a basement if you want to formalize as an ADU unit, especially if that height is further reduced by pipes or HVAC. 3)Ingress/egress is an issue for renting, as is that any bedroom also will need two (ie operable window/doorway).

I'd be happy to go over any loan questions you might have, so feel free to reach out anytime!

If so, they receive $500k tax-free capital gain after living there for 2 years.