With regard to giving a tenant leeway, its very short sighted to evict a tenant with a VERY strong track record for a VERY small shortfall one month, especially when they have been communicative and given you what sounds like a reasonable explanation as to what is going on.

The key here is open, contractual communication.  

For those STR operators and investors that are not comfortable self managing (communication with tenants, scheduling cleaners and organizing supplies) one option is to hire a designated full/part time employee. 

The contracto I used needed baby sitting and the attention to detail was lacking so half way through the reno I was more particular and communicated my expectations clearly and ofter Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

We contact them weekly using different forms of communication - email, text, calls, and mail.

Poor communication from the PM, poor subcontractors that had to come back multiple times to fix what they didn't do correctly the first time, delays upon delays with materials deliverables. 

I am documenting everything, emails, texts, communications between contractors, insurance, etc.

@Nichole Rich Byrne  I would definitely escalate communications with VRBO.

@Tony Kim I think you`re just looking at the allocation of money strictly from a Return on  "investement" (being a poor investment), where as the point of a Life Insurance/Living Benifits policy. what your Paying for is in case the individual becomes incapacitated/ has an Illness or Dies, there is a large sum of money that the family receives (and would not otherwise have) to help pay for expenses associated with the unfortunate event, and being able to carry on with life with less of a financial burden compounded with the emotional burden . being able to have retirement money liquid is icing on the cake. 

Rarity is the amount of emotion that people get when they see your post.