To my knowledge, STRs do not qualify for the real estate professional status as they are seen as a business venture and not real estate activities (this is why it is a "loophole").

I have no intention of quiting my W2 and just want to invest where I will get some extra cash for kids activities without eating into family time.

As a local investor and agent here in Columbus, let me know if you have any questions or want to connect!

I invest locally and in a judicial state, which is more difficult to foreclose. 

Market Adaptation: What unique strategies have you developed to adapt to your local market's conditions?

Certainly there are a lot more hoops to jump through disclosure wise and HR generally frowns on it fin some cases.Brokers at entrepreneurial shops (usually a local company that is privately owned or by a few partners) typically buy deals themselves a lot more.

I want to start local then work my way out from there.

Still looking for someone that is available (ideally local or near to downtown Suffolk) for small jobs and such, that can take care of things that I cannot attend to. 

Or is it 10am in both places local time?

Hire an attorney and call the local DA.