They visit annually, for years and would do so more frequently if they could avoid the cost and inconvenience of booking an AirBnB each time, and arrive to their own HOME without packing on short notice. 

Currently, the property is rented at $2100/month.The house, built in the 1900s, requires significant renovation, and the tenant frequently requests various repairs and maintenance, such as duct cleaning and appliance upgrades.

What varies is labor, which is frequently lower in a small town. 

Also, a hot water heater can be working perfectly fine, but if it's over 15 years old, that is also now an issue for many carriers.I also frequently run into situations where even if in the electrical panels there is cloth wiring over copper, the underwriters are sometimes still paranoid and assume it's cloth over aluminum.

Also, if the tenant turns over frequently you could upgrade the property management company to be a little more optimal.My biggest concern when looking at markets like this and smaller is tenant pool and supply of rental properties. 

Hello,First post but frequent visitor to these forums.  

We see this frequently.

Our family brokerage has been based in Chattanooga for over 30 years, and I am frequently at our satellite office in Nashville where I lived and invested for 4 years and still help clients.

Plus you are great leaners and understand real estate is a business of continual learning.Nice thing too for you, is that you have a built in network of high income earners that can afford to buy and maybe move frequently. 

If for example a tenant contacts you on your personal cell despite being instructed to use your work number, politely remind them, conclude the call, and then return their call using the work number.Next, create a standard operating procedure with frequently asked questions and refer to it before and during a tenancy.