Past tense.

But I can tell you that on average over the past 3 months we have brought in around 8k and this month over 10k in airbnb bookings.  

I believe the appreciation has been great over the past couple of years and prices are lower than in major areas like Miami metroplex or Charlotte.

In the past few years I've had some larger tax billed at the end of the year and I'm brainstorming ways I can reduce that burden.If I'm able to pay of our primary residence or a rental property, which should I choose?

Not sure why that happen, however the best way to screen a potential tenant is to see how they have performed in the past. 

If you really have gone from 3 to 200 properties this past year while having a two W2 jobs, you seem to have found your niche and doing well, good for you. 

Trust me, everyone is going to point the finger at someone else, and if you get involved likely the finger will be pointed at you by both parties.Send the message and let them know that this behavior past a certain time is not allowed and obnoxious before at anytime of the day violates the tenants rights. 

Analysis paralysis can definitely be tough to get past but you got this!

In the past when you called, you got a touch one for billing  touch two of whatever touch three for tech support.

I would look for investments with owner financing to skip past that requirement.Maybe you can partner with your parents on the first property?