@Martin Nussbaum @Jason CollinsIt is important that you work with tax professionals who understand the unique tax consequences and planning opportunities surrounding STRs.If the average period of customer use is seven days or less (which would encompass nearly all AirBNBs, VRBOs, etc), the rental is not considered a rental activity under the passive activity loss rules.What this means is that whether one is a real estate professional or not does not matter. 

It seems like the local meetups can be hit or miss on the quality of people you can find yourself surrounded by.

They don't want to be close to it or 15 minutes away, and especially not in a surrounding that's unattractive.

You can use online resources, such as hospital directories or real estate websites, to gather information about the location of hospitals and the surrounding area.Analyze the demand: Look into the demand for rental properties in those areas.

I have been in Real Estate in Chicago and surrounding suburbs since 1994.

As well as the surrounding areas like New Braunfels, Boerne, etc. 

Dave,Surround yourself with mentors. 

I want to build my network and find better deals in Philly and surrounding areas.

My advice would be pick ONE strategy, read as much as you can on the topic (like flipping or house hacking), then surround yourself with people who are actively doing what you want to do successfully.

For example, if I need a tub surround replaced, they get paid $125 (I supply all materials, so it's strictly labor).