You can create customizations based on what you want to have your average pricing at, set min length of stays beyond a specified # of days, etc.

He would like to sell the property while minimizing his tax liability, which ideally would be an additional land contract to our company. 

Not an ideal deal. 

If you've saved enough, trying to house hack a local 2-family in your junior or senior year (maybe with a parent as a cosigner) would be ideal because you can learn landlording and experiment with your friends as tenants.

Ideally all these LLCs should be in a state like Wyoming, Alaska, or Delaware. 

Just like everyone out their who are  Big company's like Walmart, Target, etc. have daily issues with customers that need to be resolved in person or online or complaints with the BBB. 

Have good customer service?

Got the same, poor customer service.

that I think likely you can outdo Google customer service, haha.

Ideally, the right company will handle everything from cleaning and booking management to on-the-ground troubleshooting for guests when needed.