(My transparent advice) The biggest question is, WHY would you want to entertain an offer from one of these companies?

In addition to the workmanship, you want to work with someone who is good at managing time, people and his relationship with you, his client :-)    We are actually building out a network of approved contractors because one of the biggest pain points investors and landlords face in Philly is finding reliable solutions. 

For many investors, one of the biggest challenges is scaling.

I am also aware of doing a 1031 at some point.My biggest question is taxes if I were to sell.

You can definitely buy in all cash here in Chicago or anywhere, however, one of the biggest advantages (in my opinion) in real estate is using leverage.  

Here is one of the best 1031 hacks. Lots of people complain about the "timeline" risk.Start looking for a replacement property during the marketing process of the property that you are selling.The 45 day ID period onl...

The biggest being the leaky basement but I was able to persevere. 

What is the biggest hurdle you face right now?

North Texas is good, we do deals there and in Ohio, Cincinatti, Missouri, Michigan and my personal FAV Indy.My biggest suggestion is to screen the TEAM more than the area, make sure they can deliver a specific result.  

Honestly, the biggest challenge in your market won't be finding deals, it will be over regulation and lack of control over your property.