I don't think this necessarily needs to be done right away. If you want to give some time between the satsraiser and this we can wait a couple weeks or a month. Maybe next week do a poll to see if the community is interested in the idea and then do another one to see who they want to roast. Make sure that person is cool with it and set a date.

I like the idea of something like this or a memeathon or a share your best jokes day kind of events as complimentary almost mini-satsraisers that are fun and hopefully drive some engagement for SN and raise some sats for charity.