Does anyone have any good questions they might ask that might reveal some good information about the market in general, jobs, housing, population...I'm open to any suggestions.  

If you work hard on your site, build backlinks, engage in regular "social signals", keep your site up-to-date with fresh content, you will climb.Although Google does change its algorithm overtime, the trend has been to make "technicalities" less relevant.  

Condos and duplexes have associations, many of which restrict the number of units that can be rented or outright prohibit (generally small associations - 20 units of less).Everyone wants to purchase a condo in the areas you're considering and unless you are drilling 100k fresh out of school, you may not qualify based on your income alone. 

All in all what I'm hearing is the most I could reasonably do is reach out to the owner to sell, receive info on their operating expenses and rent roll, informally negotiate good terms and price, maybe even go so far as a non-binding LOI, and then pass it on to another investor till I'm fresh out of clout even for off market.

It would probably reveal some cool insights, it would help deciding on which model to use for prediction, and it could also help with anomaly detection (for data cleaning and/or finding potential deals).

A simple google search reveals neighborhood info or you can buy the house spur of moment with no insight and Be upset with the sales person for your lack of research.

A deep clean, fixing any minor items, and maybe a fresh layer of paint usually does the trick.

Sheen is my biggest thing since semigloss cleans well but flat hides imperfections and rarely do I have fresh/smooth walls.

The walls were professionally freshly painted before they moved in and now they're thrashed.

Looks like the only thing it needs is a re finish of the wood floors and maybe some fresh paint.