Over on Bluesky, Molly Shah just ran a sweepstakes to raise money for Jamal Abu Hashem to escape Gaza. It went really well: 70 community members donated prizes and we raised 10,000 pounds.
I talked to Molly and she said that she's willing to share the google forms and other backend details that she used to run the sweepstakes and do a bit of hand-holding to get other similar fundraisers off the ground.
I am not in a position to run a contest like this myself but if you're interested in running one for your community, please either get in contact with Molly on bluesky (mommunism.bsky.social) or twitter (mollyoshah) or, if you aren't on those websites, send me an ask with your email or discord and I'll connect you.
Some communities that I think would be really good at this kind of thing include pretty much any fandom (furry commission prizes anyone?), assorted social media communities (cohost, mastodon, pillowfort, etc), specific interest groups/hobby communities (ttrpgs, gaming communities, retrocomputing, etc), and streamers.
Molly has a pretty well vetted group of families in need ready to go. Please reach out if you're interested. Thanks.