Additionally, I expect applicants to follow instructions in the advertisement and application, to make and keep appointments, to show up on time for appointments, dress and behave appropriately at appointments, and in general demonstrate throughout the process that they are someone that is easy and pleasant to do business with.

It really depends on what you are looking and I think your thought process is correct.

This ensures that any payout for damage or liability can be processed more smoothly, and it can help protect your interests if something happens on the property. 

I am looking to make a couple connections now during the moving process.

I think smaller markets say sub 50k population would have a larger impact from one big move from a manufacturing facility or something like a Amazon processing center.

If you are not looking to evict now, I'd wait with these types of tenants until closer to the 30 days, you are looking for more confrontations and problems if you tell them you won't renew. if anything,  you can say that if there will be another violation you will start eviction process best of luck 

I'm trying to analyze my first property and not sure how to set it up to run the number using the calculator tools here. 2 of the units are successful Airbnb short term rentals, and the other two units are month to month rentals to existing tenants.

@Bridger L Logan I’m doing this in CO Springs with tremendous success.

Trade some comfort for financial stability.Part of attaining financial success is being simultaneously optimistic and paranoid. 

It's the simplest way and walks them through the entire STR process.