My property manager handles the majority of my repairs, etc.  

I believe it appraised without issue.

Sure, it's minorly annoying ... but if I got a call from someone who was able to solve a big problem for me and was nice and polite all the way through, I would have absolutely no issues with that.

The issue from my perspective is that the contract is unsecured.

By using a email collection service like “Emailcollect” you can inexpensively get past guest data and send out a monthly touch point about something that’s happening locally without it becoming a major drama of making up newsletters. 

Typically, a PMC issues monthly owner statements.

@Christopher Davis my property manager does an inspection about 30 days before lease end, verifies timeline with current tenant and potential turnover issues.

Is it a headache or is there any type of legal issues with this method?

At the end of the year, I share that sheet to my accountant and he does my accounting without any issue. 

And there is a particular cutoff per geographic region.In our specific case, our property is less than 15 minutes away from 2 golf courses, and 20-30 minutes away from 2 major lakes, 30 minutes away from Rocky Mountain National Park, etc.