You can still swing by your parents place for the occasional free dinner :) Kudos to you for starting so young.

And keep your handyman on speed dial because there will be plenty of occasional electrical and plumbing and HVAC and hot tub issues, many of which will be minor but will still require your handyman to take a look.

To clarify, I'm not talking about property managers, but rather teams focused only on regular ongoing maintenance, emergency services and/or the occasional site check.  

I'm going to be the one messing with the software most of the time but my wife will be helping occasionally.

I'm still getting the occasional call or text message four years later.

We have a 1/1 so it's sufficient since we usually only have 1 guest at a time, occasionally 2.

The idea of buying a property in Big Bear is that our family can stay up there occasionally when it is not rented out.  

Cushman in my market primarily lists through their website, but occasionally will put something on Loopnet.  

You will occasionally see good listings in Owings Mills/Reisterstown area.

As far as "affluence", goes I'd rank the areas as follows:1) German village/Bexley2) short north3) Olde Town East4) Franklinton5) South of Main6) Linden7) HilltopHowever, Franklinton is great to live in, like anywhere.... don't leave your laptop in your backseat overnight, and you hear the occasional gunshot, but honestly that's anywhere close to downtown.That's just my opinion from living in the city for almost 10 years and living in two of the mentioned areas.