-what do you think about my goals, is it feasible?

I'm not sure where to look to find the data needed for a feasibility study for a specific area. 

Driving around isn't feasible.

Chicago is the 3rd largest metropolitan city with 10 million occupants. 42% or 4,200,000 are renters so it's great to know the exit strategy of selling to an end user is feasible.

A snapshot feasibility report gave favorable figures for med / healthcare services are on uptick in my area. 

On an average deal, using median housing price in the US for instance (and depending on where you are investing), net of $28,000-$30,000K is feasible per flip deal.

Long distance investing can be a challenge but as long as you have a good team or PM company managing your property it certainly is feasible.  

The last few years have made the front range less feasible for investing for cashflow.  

This was a bit different for them so I gave them my analysis of the feasibility of such a project.  

what has changed that this would even be a consideration, You don't have to say yes.. if it's because the house is no longer feasible to suit there physical condition, due to access or other features I may agree to looking but the funds can also be used to remodel and upgrade current house to fit their needs.