Know of any good videos for tourism, documentary, or otherwise that can educate me on Madeira? Know absolutely nothing about it and I had to look it up on a map.

Also, what is the annual weather conditions like there?

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haha... the south side of the island is literally perfect sunny weather all year around except october to march it rains a little

a lot of locals know english, because of the tourism, and also because a lot of them either resettled here from south africa about 20 years ago or they are younger ones who went to work in the UK, literally every young person on this island i have met speaks like a londoner lol

it's a very rugged landscape, and outside of the dense urban areas around the capital funchal it's mostly farmers, and practically anywhere beyond 10 miles from the centre of funchal you are likely to be walking down a street and hear goats or sheep bleating, as there is a substantial market of especially goat milk to make cheese here

you need to have a car, pretty much, unless you are a crazy mofo like me i have got by for about 15 months on foot and bicycle, and the buses are terrible, but not that expensive, but expensive, because actually the ripples of the landscape make travel very slow between places that look close on the map

not sure what else to say about it, but for sure you could probably settle yourself here, especially if you can get your hands on a european passport, that would be a piece of cake