Just felt comfortable with him. 

Perhaps when you are comfortable you know what you are doing.Paul

Then there are those who are comfortable investing in bad neighborhoods and know how to make it work. 

Are they comfortable investing for a period of time or are they looking for shorter-term investments?  

So I feel comfortable that that particular listing has folks involved with expertise in this area.

Wouldn't a motivated seller feel more comfortable letting me into their home if its me that they initially talked to?

As to your question in depends on your comfort zone . 

That's comforting to know as there are some nice properties up and down that area from the airport right up to Target field.

Now you have the personal credit card debt gone, you have substantial cash still left to buy another rental house if you like, or hold for a year or two and buy another quad-plex.My concern here is you build it correctly from the beginning, don't be saddled with the debt and things that are a burden when you can start fresh with a much more comfortable trajectory.

@Ashley Pittman It is okay to go slow, and figure out what you are comfortable with.