This was incredibly frustrating because I must have called 15-20 contractors and after having 6-10 come out to the job site with me to give me an estimate...I received a whopping 4 estimates.

I tried to reply before, but it was very glitchy on my iPad & I got frustrated...

I tried my luck at the Forth Worth \ Crowley Texas area, but was very frustrated after putting in offers on multiple properties on the MLS, getting accepted by 2 and both deals falling through ( 1 for over priced home, would not appraise and the other for finding out only after inspections that one of the tenants was a HOARDER!

Go at your comfort level for I can tell you from experience that if you start feeling you are in over your head with too much work, not enough capital, and contractors messing around with you, your energy for continuing on a path of real estate investing turns in to complete frustration. 

If your frustration comes out at him in a negative way, it will make him more likely to avoid you and less likely to satisfy your need.If his wife, or other family members, have indeed been hospitalized recently, then that is an understandable source of distraction.

When you hire your agent make sure they provide you w/ the latest sales statistics for Pilsen so you don't get frustrated when you start making offers.

Austin,I understand your frustration however you have to look at it from the realtors prospective.

Also, they usually get frustrated if you don't move on a property because your cap rate goal is higher than theirs.  

I want to know what has been your biggest problem, frustration, or just a lack of knowledge in getting started with investing in real estate.

Don't get frustrated , just keep bidding your best and highest offer.