I suggest doing your own research for data and assumptions (like rent, vacancy, appreciation/depreciation, etc.) and not rely on AI. 

Might be a little bit down the road for me, but that is for sure dream that will come true...One Chicago's best features is the lake, which I'd like more access to.

I am new to real estate investing and BP, and I am excited to learn more about this space!

Or will i need to have $35k + reserves of my own money to make this happen?

For example on a SF purchase you're probably at a 60% to 65% LTV and around 6.99%. 

John I rented a 4 plex i remodled in charleston as the flip market had slowed.. the tax's on it were substantially higher than an owner occ property.. could be the rates were different this was a 1.2 mil prop..

It is maybe a couple thousand dollar up-front cost for the developers to determine the viability of a project.I work with experienced developers, who could perform & gather all this data on their own if they really wanted to, but the value that an engineer brings on these is typically worth their time & small cost. 

First time on this forum, and just introduced through two books I just read by David Greene and Brandon Turner.  

Do you handle this through the platform (AirBNB or VRBO) or outside?

In addition to STR'ing the main house, he is building 2 more units (ADUs) on the back side of the property.