This is definitely something that could work better, as it would be accessible for people in their homes, and less expensive. It would be interesting to offers my options in a augmented reality option as well (eg. create a community of traveller, prepared interviews of the loved ones, allow client to assist to a concert etc.)
I like the idea !! Finding someone to achieve the bucket list with you definitely help. This made me think of 100 things from Sebastian Terry: http://100things.com.au/ Have a look I'm sure you will love it.
You're idea could take the form of an collaborative economy platform such as StokeShare (which connects mentors with young adventure lovers).