I guess you could (over time) influence the prevailing cap-rate but I think that would take longer.

all these could influence where its a gem or rock and what youre prepared to offer5.

Read Grant Cardone's books, study how to Invest in Real Estate with no and low money down from Brandon Turner, how to negotiate from Chris Voss, how to pick a market and Syndicate from Joe Fairless, how to build a brand and raise capital from Hunter Thompson and Matt Faircloth, how to Win Friends and Influence People from the book by the same name. 

Don't get me wrong, I'm sure you are a great dad, but if he is anything like I was, I was a typical teenager who was thirsty for new influences in my life (not just my parents). 

Networking will greatly increase your probability of a successful investor, and a good network of agents, lenders, PM's, and contractors in your target market will greatly influence your success as an investor.

In the middle...there's a lot more going on to influence values.

ScottThe One Thing – Gary KellerThe Fountainhead – Ayn RandHow to Make Friends and Influence People – Dale CarnegieAwaken the Giant – Tony RobbinsThe War of Art-Steven Pressfield2.Start networking.  

Since you live in the south suburbs you probably have a better idea of which areas there are more desirable for renters but of course proximity to public transportation, restaurants, schools, etc can influence your ability to reduce vacancies.

Could this challenge influence the price I sell the building at, if I decide to sell it ... let's say a couple of years from now?

I have seen people caution about the "Guru Way" and the influence but I am honestly not finding resources to learn from.