What type of situation would a first time investor be in?

We have collaborated with Hemlane to do a lease-up for an OOS investor.

I've seen other investors get into these types of deals based on potential income.

At least 25% and some investors I know locally making up to 1000% per year. 

Investors are tripped up when the prior owner changes the use without permitting the changes and in those instances a rental license is not attainable for the new unit counts.

So would you say that living independently was very transformative and a critical step in becoming the investor you are today? 

For any investors who are knowledgeable about these areas or are currently active here, are there any particular neighborhoods, zip codes that stand out as good starting points.

In the Tax Sales and Sheriff Sales, its even worse as you usually can;t get inside, unless some other "investor" has already busted the door in. 

The wholesaler isn't a competent contractor or even a competent investor themselves 99% of the time, so you have to decide who you want to rely upon for estimates.

@John Clark brought up a great point...here in Chicago, you can not deny based on criminal record, so you may want to double-check Balitmore's rules and regulations.Also, double-check if your verification system localizes the search or if it is nationwide.I'd consider checking with some of the larger property managers or investors in your areas to see if they have similar issues.