Does that mean it's a market I should or shouldn't even bother?

I would recommend to just start attending some of the large player's conferences and networking your way into a relationship there.

I self manage my rentals and I don't currently have a job, so it hasn't bothered me yet having them more spread out.

All my documentation, driver license, mail etc has the property A address, I never bothered to change anything when I purchased property B.

I am currently going to attempt to use VLC player to listen to them.

I guess what bothers me about this "hobby landlord"  phrase is it tries to demoralize folks instead of teaching them. 

So, assess your risk tolerance and you may want to do some research on if there's any sort of gap policy or policy you can obtain temporarily - Proper Insurance and CBIZ are the two major players in the STR insurance biz, but I'm not sure if they write anything other than a full policy.  

They were players with nothing to lose and I was an idiot.

Here's why the confusion bothers me. 

- If I were holding the property as a rental, I wouldn't bother alerting the taxing district the additional SF.