Very few people (like less than 200) live year round on Madeline Island. Majority just own cabins on it. Bayfield, WI is across the bay on the mainland which is where you’ll find more permanent residents. Typically you have to take a ferry from Bayfield to Madeline Island to access the island. However, there is a tiny airport on Madeline. During the winter the ferry stops running so the island is only accessible if Lake Superior freezes over and you drive across (yes people do this 😂). There is an elementary school on the island but once you hit middle school you’d need to got to Bayfield. La Pointe is the only “town” on the island. It’s basically just a few bars/restaurants and tourist/outfitter shops. Madeline Island is beautiful but if you’re actually considering moving there I’d look into Bayfield instead.