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.

If you feel comfortable with a handyman with enough experience, you may be able to get away by going that route and have him act as the GC in the process.

If you're coming over for fun, then maybe the city museum for an adult night might be in order... but bring your running shoes :)

Start small and pick a pace you're comfortable with (1 a year, 2 year, etc).

Honestly, I'm not sure I'm comfortable with her having keys.

We are not in a place financially where we feel comfortable investing (yet).