Looking for sites that are well positioned around areas of growth within close proximity of universities (to capitalize on student population) medical centers, technology districts, financial districts, area entertainment and outdoor recreation, trail systems & transportation options. 

It shows how poor the wider transport network is to an extent--even widening out to 45 min doesn't expand the map as much as I thought.

Growth here is quite immense given the recent drive of transportation, logistics, and distribution and we only see that demand growing as the internet grows as well. 

Look here: Overview of Individual Taxation in Switzerland I have done a quick side to side comparison of the cost of living in Chicago vs Zürich and while on the surface it seems cheaper to live in Chicago, I've found it not to be when one factors in things like insurance, transportation, quality of life, commuting times and so on.

Given that we visit my family in Mexico sometimes so the transportation is not of a big concern, do you see any issues with it?

A lot will depend on the condition of the home and its relative location to certain amenities (shopping, transportation, entertainment, etc). 

Of course, you have to eat, cover transportation costs, and keep a roof over your head as well.  

Cities determine the zone for properties based on long term strategies, tax base, transportation, density, etc. - and so changing the zoning of a property from Commercial to residential doesn't generally result in a lot of success.

And you’re basically running an unlicensed and unregulated hotel. why wouldn’t you just let the person keep living there and rent the rest of the units as short term?

The most important factors in achieving the results you expect will come down to location of the property in a market; how that property is renovated before being put in service; and finally how it is managed.Many investors pay close attention to transportation services, crime reports, school reports, etc.