Seems easy enough to get a dedicated Ventra card and load it with some funds to allow for easy traveling throughout the city. 

I am a Real Estate Broker and Investor who does not have enough time to dedicate to calling expired/fsbo/cancelled and lists of distressed homeowners.

be proactive, be polite, enthusiastic and dedicated.

We have a Short Sale Forum dedicated to this topic.

Dedicate that time and energy to finding more leads!

Until you have the time, dedication, skills and background, just accept the fact you won't be learning financing.

Look into Hard Money or Private Money LendersFind a hard money lender or a dedicated hard money broker who knows all the real lenders from the bogus lenders.

That amount, with some hard work and dedication is attainable, and will be something that I can achieve this year.At 26 years old, if start investing into my future now, I will be able to buy the next one in a couple years, and within about 5, I should have enough saved up to buy something ( possibly out of state) in cash rather than having to finance it. 

BP itself has dedicated sections to REO's - with the rule of thumb of never buying above 30% of list.How does REO investment work? 

The residential market might be faster but I would dedicate at least a year of hard work before thinking about readjusting or pivoting to another industry.