Upselling to guests-as a business?

[Julie Groth]

Does anyone upsell to guests as a systemized business model? You know, travel insurance, art work, local restaurants, special cake delivery, laundry service (for their kids at college), car service, special events, etc...etc.

I know someone who is hiring a full time person to manage just this aspect (so, it will cover their salary plus make money). 

Is it worth it? How much upside is there?