And also, once I do find a property I want to pursue I am thinking hard money may be the best bet for me with where I’m at at this point in my career.

is it bad? 

The trouble with bad agents is that they don't realize they're bad, and they're the ones who would make a stink about something like that... 

Depending on the class of tenant, you may need to up your vacancy percentage and you may have some "bad debt" (rent that is never paid). 

When performing a quick preliminary screening on those websites (i.e. to exclude obvious bad deals), do you usually use the 50% rule (or similar % rule) to estimate expenses?

In my experience, bad GC's typically front-load the SOV with all of their profit.

This will be very hard to resist in the early stages of your career.

Upon closing and finalizing the loan, I realized the mortgage / taxes / insurance / PMI totaled out to $640 a month, which isn't bad in my opinion, but a little more than the $550 I was hoping for.

It's not that hard, but if you've never done it and are nervous, it's not a bad idea to hire a realtor to walk you through it.2) You pay a title company to research the title and get title insurance, same as if you used a realtor.3) Not really - but like you said, guidance and knowledge are worth a lot.

Hello, I am looking to get started in my Real Estate career by building a 3 Unit Condo complex on a lot that I already own in Chicago.