In theory this sounds like  this deal could be done just as easy at a trailer park that allows renters and do away with transportation cost.  

I prefer relatively safe, urban neighborhoods with a high walkability quotient afforded by a commercial avenue or two and access to public transport. 

What if I told you it would be a good idea if you worked at a full time job, and then started to work on a side job...paying your employer, and this was fine with you because your first job gave you more money than you knew what to do with, and you "hoped" that the side job would give you a promotion (apartment conversion), transfer you to a closer location saving transportation costs (tax savings) and give you a raise (rent increase) but you didn't know when/if yet?

-BSEE from UT-Austin-MBA from TCU (Lockheed Martin paid for it....every cent)-2 years training in real estate from specialized niche training program (worth every cent)-10 years in corporate world (transportation industry, designed fighter pilots control systems, designed automated test equipment, tested computer software)-10 years of real estate experience now (SFRs, multi-family, fix/flip, new construction, small development, ran coaching program for almost 2 years)Finance coursework has proved very useful as has the MBA training.

Perhaps too impulsively, I invested 20k to set up an Airbnb in an HOA governed neighborhood: one of the few left unregulated outside of Boulder, CO, and the neighbors just informed me that there are several clear rules I am breaking with my Airbnb Ads, he has found them and requested I stop at threat of calling in the HOA. 

- Transportation/commuters- Quality of life/neighborhoodEtc.

At the time, they had no transportation, only the girlfriend had a valid drivers license, and neither one of them had a job.

Need reliable transportation for those days.

If I were you, I'd buy a SFH in a neighborhood with good public transportation to get to the Loop.

I am confused on whether to purchase a 2bd/1bth condo in a gentrified area close to public transportation or purchasing a 3bd/1bath condo in a "ok" established neighborhood.