We lived in the outer Hebrides for 10 years and still own a house there, we spend several weeks a year up there and plan to retire there too.
The weather is interesting, can be sunny in one part of the island and raining 20 miles away. Midgies are more of an issue than the weather. We just bundle up in good rain gear and go out anyway. Where we lived there were 5 buses a day to Stornoway (I don't drive for medical reasons) but it's only half an hour by car, and there's a Tesco there that delivers.
We moved to the big city 18 years ago now, but still consider Harris to be "home", as do our children. We found getting things delivered quite difficult, and the best way was to get things delivered to the haulier in Inverness who would then bring it over. Royal Mail you need to add an extra day on to the posting time. Health care was good, including flying me to Inverness with pregnancy complications, and schools also good. Little to do for teenagers unless very outdoorsy or interested in sheep!
Gaelic spoken widely, even by some of the younger generation, and a thriving traditional music scene. Great festival in the summer. Our dc regard themselves as native speakers and were educated in Gaelic at the Gaelic school in Glasgow. Very big on ceilidh dancing and musical performance.
There's trouble in getting housing now, as a pp said there's a lot of holiday lets and it's a struggle to get on the housing ladder, partly because of rising costs but often there just aren't enough houses. Jobs are mainly in the council and the health board.
We're going up next week. I can't wait!!