Right now, I'm just looking to supplement my income and save money to enhance my RE porfolio.

Maybe you can use the money your earning as teacher to help supplement a marketing plan that will enhance what you are already doing so you can build a bigger network closer to where you live. 

I also love what I do and am not currently looking to replace my day job but instead use REI to enhance our digital nomad lifestyle while building long term wealth.

It’s called enhanced coverage (each insurer may have a different branded name) and the premiums are approximately 20% higher.  

Future enhancement I’ll just hope they add I guess...

They're going to tell you just how they feel about your (insert favorite sentence enhancer) marketing tactics.

Any tools out there that could automate the listing description?

Keep massaging it. 

Weekly Supp. 513a, (Orange County Court, 9th Judicial Circuit, 2013).It is the intent of the Florida Legislature that consumers be encouraged to retain competent legal counsel to protect their rights as tenants not only for their direct benefit, but for the indirect benefit of all consumers/tenants.The Court found that it is appropriate to award a risk enhancement multiplier.

Sell the property with inherited tenant to a bulldog who can deal with the tenant who is entitled to you treating them to a massage, craft beers, acrylic nails and hair to be done every week.