However open and honest communication is always good practice.

Then when FEMA starts to come through and the neighbors start communicating they all list their houses with one realtor for the whole neighborhood at a set price/sqft.

(I was wondering if I am just a different generation and needed to revise how I communicate).

If you establish a window of time in which you will be accepting applications, clearly communicate your process and your rental criteria from the start, it's perfectly acceptable to review a batch of applications at the same time, rank them according to your criteria and them process them one at a time until you find a suitable tenant.

If the tenant fights the charges, you should consider taking them to court to recover the cost.It's hard to know where to lay the blame without seeing all their communication.

Just curious: with whom were you communicating that pissed them off so badly? 

Honest communication about their ability and understanding of a market. 

How I have it set up it allows my tenants to know my expectations and they know to communicate with me if there is any issues with them paying on time and then that is communicated and if they fail they get a 3 day at that time.  

I also recommend you cut off all communication and start the eviction process.

If he's gone dark/hasn't been communicating, I'd say the biggest risk is that if he's a contractor, there are no wages to garnish.